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Items: 1 to 50 of 212

1.

Pushing the limits of concertedness. A waltz of wandering carbocations.

Castiñeira Reis M, López CS, Nieto Faza O, Tantillo DJ.

Chem Sci. 2018 Dec 11;10(7):2159-2170. doi: 10.1039/c8sc03567a. eCollection 2019 Feb 21.

2.

Formal [4 + 2] Cycloadditions of Anhydrides and α,β-Unsaturated N-Tosyl Ketimines.

Burlow NP, Howard SY, Saunders CM, Fettinger JC, Tantillo DJ, Shaw JT.

Org Lett. 2019 Feb 15;21(4):1046-1049. doi: 10.1021/acs.orglett.8b04091. Epub 2019 Feb 5.

PMID:
30721078
3.

Post-transition state bifurcations induce dynamical detours in Pummerer-like reactions.

Hare SR, Li A, Tantillo DJ.

Chem Sci. 2018 Oct 4;9(48):8937-8945. doi: 10.1039/c8sc02653j. eCollection 2018 Dec 28.

4.

Correction: The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

McAlpine JB, Chen SN, Kutateladze A, MacMillan JB, Appendino G, Barison A, Beniddir MA, Biavatti MW, Bluml S, Boufridi A, Butler MS, Capon RJ, Choi YH, Coppage D, Crews P, Crimmins MT, Csete M, Dewapriya P, Egan JM, Garson MJ, Genta-Jouve G, Gerwick WH, Gross H, Harper MK, Hermanto P, Hook JM, Hunter L, Jeannerat D, Ji NY, Johnson TA, Kingston DGI, Koshino H, Lee HW, Lewin G, Li J, Linington RG, Liu M, McPhail KL, Molinski TF, Moore BS, Nam JW, Neupane RP, Niemitz M, Nuzillard JM, Oberlies NH, Ocampos FMM, Pan G, Quinn RJ, Reddy DS, Renault JH, Rivera-Chávez J, Robien W, Saunders CM, Schmidt TJ, Seger C, Shen B, Steinbeck C, Stuppner H, Sturm S, Taglialatela-Scafati O, Tantillo DJ, Verpoorte R, Wang BG, Williams CM, Williams PG, Wist J, Yue JM, Zhang C, Xu Z, Simmler C, Lankin DC, Bisson J, Pauli GF.

Nat Prod Rep. 2019 Jan 1;36(1):248-249. doi: 10.1039/c8np90041h. Epub 2018 Nov 23.

PMID:
30468235
5.

A problem in the structure assignment of acremolin C, which is most probably identical with acremolin B.

Banert K, Tantillo DJ.

Nat Prod Res. 2018 Nov 16:1-5. doi: 10.1080/14786419.2018.1509330. [Epub ahead of print]

PMID:
30445873
6.

Diterpene Synthase-Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers.

Pelot KA, Hagelthorn DM, Hong YJ, Tantillo DJ, Zerbe P.

Chembiochem. 2019 Jan 2;20(1):111-117. doi: 10.1002/cbic.201800580. Epub 2018 Nov 28.

PMID:
30393911
7.

Secondary Carbocations in the Biosynthesis of Pupukeanane Sesquiterpenes.

McCulley CH, Tantillo DJ.

J Phys Chem A. 2018 Oct 11;122(40):8058-8061. doi: 10.1021/acs.jpca.8b07961. Epub 2018 Sep 27.

PMID:
30209949
8.

N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights.

Zhu JS, Kraemer N, Shatskikh ME, Li CJ, Son JH, Haddadin MJ, Tantillo DJ, Kurth MJ.

Org Lett. 2018 Aug 17;20(16):4736-4739. doi: 10.1021/acs.orglett.8b01655. Epub 2018 Aug 1.

PMID:
30067041
9.

Predicting Productive Binding Modes for Substrates and Carbocation Intermediates in Terpene Synthases-Bornyl Diphosphate Synthase as a Representative Case.

O'Brien TE, Bertolani SJ, Zhang Y, Siegel JB, Tantillo DJ.

ACS Catal. 2018 Apr 6;8(4):3322-3330. doi: 10.1021/acscatal.8b00342. Epub 2018 Mar 8.

PMID:
30034923
10.

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

McAlpine JB, Chen SN, Kutateladze A, MacMillan JB, Appendino G, Barison A, Beniddir MA, Biavatti MW, Bluml S, Boufridi A, Butler MS, Capon RJ, Choi YH, Coppage D, Crews P, Crimmins MT, Csete M, Dewapriya P, Egan JM, Garson MJ, Genta-Jouve G, Gerwick WH, Gross H, Harper MK, Hermanto P, Hook JM, Hunter L, Jeannerat D, Ji NY, Johnson TA, Kingston DGI, Koshino H, Lee HW, Lewin G, Li J, Linington RG, Liu M, McPhail KL, Molinski TF, Moore BS, Nam JW, Neupane RP, Niemitz M, Nuzillard JM, Oberlies NH, Ocampos FMM, Pan G, Quinn RJ, Reddy DS, Renault JH, Rivera-Chávez J, Robien W, Saunders CM, Schmidt TJ, Seger C, Shen B, Steinbeck C, Stuppner H, Sturm S, Taglialatela-Scafati O, Tantillo DJ, Verpoorte R, Wang BG, Williams CM, Williams PG, Wist J, Yue JM, Zhang C, Xu Z, Simmler C, Lankin DC, Bisson J, Pauli GF.

Nat Prod Rep. 2019 Jan 1;36(1):35-107. doi: 10.1039/c7np00064b. Epub 2018 Jul 13. Erratum in: Nat Prod Rep. 2018 Nov 23;:.

11.

Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C3) Sequences: Scope, Limitation, and Computational Investigations.

Kaufman RH, Law CM, Simanis JA, Woodall EL, Zwick CR 3rd, Wedler HB, Wendelboe P, Hamaker CG, Goodell JR, Tantillo DJ, Mitchell TA.

J Org Chem. 2018 Sep 7;83(17):9818-9838. doi: 10.1021/acs.joc.8b01322. Epub 2018 Jul 26.

PMID:
30001484
12.

Rearrangement of Hydroxylated Pinene Derivatives to Fenchone-Type Frameworks: Computational Evidence for Dynamically-Controlled Selectivity.

Blümel M, Nagasawa S, Blackford K, Hare SR, Tantillo DJ, Sarpong R.

J Am Chem Soc. 2018 Jul 25;140(29):9291-9298. doi: 10.1021/jacs.8b05804. Epub 2018 Jul 13.

PMID:
29968475
13.

Questions in natural products synthesis research that can (and cannot) be answered using computational chemistry.

Tantillo DJ.

Chem Soc Rev. 2018 Oct 29;47(21):7845-7850. doi: 10.1039/c8cs00298c.

PMID:
29900461
14.

Using 1H and 13C NMR chemical shifts to determine cyclic peptide conformations: a combined molecular dynamics and quantum mechanics approach.

Nguyen QNN, Schwochert J, Tantillo DJ, Lokey RS.

Phys Chem Chem Phys. 2018 May 23;20(20):14003-14012. doi: 10.1039/c8cp01616j.

PMID:
29744489
15.

Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase.

Jia M, O'Brien TE, Zhang Y, Siegel JB, Tantillo DJ, Peters RJ.

ACS Catal. 2018 Apr 6;8(4):3133-3137. doi: 10.1021/acscatal.8b00121. Epub 2018 Mar 8.

PMID:
29713562
16.

Biosynthesis and Conformational Properties of the Irregular Sesquiterpenoids Isothapsadiene and β-Isothapsenol.

Cool LG, Vermillion KE, Takeoka GR, Wang SC, Tantillo DJ.

J Org Chem. 2018 May 18;83(10):5724-5730. doi: 10.1021/acs.joc.8b00800. Epub 2018 May 2.

PMID:
29684282
17.

Bioinspired synthesis of pentacyclic onocerane triterpenoids.

Bartels F, Hong YJ, Ueda D, Weber M, Sato T, Tantillo DJ, Christmann M.

Chem Sci. 2017 Dec 1;8(12):8285-8290. doi: 10.1039/c7sc03903d. Epub 2017 Oct 16.

18.

A Maze of Dyotropic Rearrangements and Triple Shifts: Carbocation Rearrangements Connecting Stemarene, Stemodene, Betaerdene, Aphidicolene, and Scopadulanol.

Hong YJ, Tantillo DJ.

J Org Chem. 2018 Apr 6;83(7):3780-3793. doi: 10.1021/acs.joc.8b00138. Epub 2018 Mar 22.

PMID:
29494166
19.

Prediction of 19F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

Saunders C, Khaled MB, Weaver JD 3rd, Tantillo DJ.

J Org Chem. 2018 Mar 16;83(6):3220-3225. doi: 10.1021/acs.joc.8b00104. Epub 2018 Feb 26.

20.

Premutilin Synthase: Ring Rearrangement by a Class II Diterpene Cyclase.

Xu M, Jia M, Hong YJ, Yin X, Tantillo DJ, Proteau PJ, Peters RJ.

Org Lett. 2018 Feb 16;20(4):1200-1202. doi: 10.1021/acs.orglett.8b00121. Epub 2018 Feb 1.

21.

Coupled Electrocyclization/Prototropic Shift in the Biosynthesis of Crotinsulidane Diterpenoids.

Campos RB, Tantillo DJ.

J Org Chem. 2018 Jan 19;83(2):1073-1076. doi: 10.1021/acs.joc.7b02904. Epub 2018 Jan 9.

PMID:
29272127
22.

Synthesis and Structure Revision of Dichrocephones A and B.

Schmiedel VM, Hong YJ, Lentz D, Tantillo DJ, Christmann M.

Angew Chem Int Ed Engl. 2018 Feb 23;57(9):2419-2422. doi: 10.1002/anie.201711766. Epub 2018 Jan 16.

PMID:
29251825
23.

Diverged Plant Terpene Synthases Reroute the Carbocation Cyclization Path towards the Formation of Unprecedented 6/11/5 and 6/6/7/5 Sesterterpene Scaffolds.

Huang AC, Hong YJ, Bond AD, Tantillo DJ, Osbourn A.

Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1291-1295. doi: 10.1002/anie.201711444. Epub 2017 Dec 28.

24.

Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach.

Lim NK, Weiss P, Li BX, McCulley CH, Hare SR, Bensema BL, Palazzo TA, Tantillo DJ, Zhang H, Gosselin F.

Org Lett. 2017 Nov 17;19(22):6212-6215. doi: 10.1021/acs.orglett.7b03141. Epub 2017 Nov 8.

PMID:
29115843
25.

Correction to "Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction".

Zhu JS, Son JH, Teuthorn AP, Haddadin MJ, Kurth MJ, Tantillo DJ.

J Org Chem. 2017 Dec 1;82(23):12946. doi: 10.1021/acs.joc.7b02695. Epub 2017 Nov 1. No abstract available.

PMID:
29091433
26.

Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Zhu JS, Son JH, Teuthorn AP, Haddadin MJ, Kurth MJ, Tantillo DJ.

J Org Chem. 2017 Oct 20;82(20):10875-10882. doi: 10.1021/acs.joc.7b01521. Epub 2017 Sep 28. Erratum in: J Org Chem. 2017 Dec 1;82(23):12946.

27.

Correction: Dynamic behavior of rearranging carbocations - implications for terpene biosynthesis.

Hare SR, Tantillo DJ.

Beilstein J Org Chem. 2017 Aug 15;13:1669. doi: 10.3762/bjoc.13.161. eCollection 2017.

28.

Elucidating Substrate Promiscuity within the FabI Enzyme Family.

Freund GS, O'Brien TE, Vinson L, Carlin DA, Yao A, Mak WS, Tagkopoulos I, Facciotti MT, Tantillo DJ, Siegel JB.

ACS Chem Biol. 2017 Sep 15;12(9):2465-2473. doi: 10.1021/acschembio.7b00400. Epub 2017 Aug 31.

PMID:
28820936
29.

Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin Meroterpenes.

Xu G, Elkin M, Tantillo DJ, Newhouse TR, Maimone TJ.

Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12498-12502. doi: 10.1002/anie.201705654. Epub 2017 Aug 30.

30.

Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides.

Mendoza-Sanchez R, Corless VB, Nguyen QNN, Bergeron-Brlek M, Frost J, Adachi S, Tantillo DJ, Yudin AK.

Chemistry. 2017 Sep 27;23(54):13319-13322. doi: 10.1002/chem.201703616. Epub 2017 Aug 31.

PMID:
28771904
31.

Biomimetic Platinum-Promoted Polyene Polycyclizations: Influence of Alkene Substitution and Pre-cyclization Conformations.

McCulley CH, Geier MJ, Hudson BM, Gagné MR, Tantillo DJ.

J Am Chem Soc. 2017 Aug 16;139(32):11158-11164. doi: 10.1021/jacs.7b05381. Epub 2017 Aug 3.

32.

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.

Xu Y, Hong YJ, Tantillo DJ, Brown MK.

Org Lett. 2017 Jul 21;19(14):3703-3706. doi: 10.1021/acs.orglett.7b01420. Epub 2017 Jul 7.

33.

Mechanism of a No-Metal-Added Heterocycloisomerization of Alkynylcyclopropylhydrazones: Synthesis of Cycloheptane-Fused Aminopyrroles Facilitated by Copper Salts at Trace Loadings.

Wilkerson-Hill SM, Yu D, Painter PP, Fisher EL, Tantillo DJ, Sarpong R, Hein JE.

J Am Chem Soc. 2017 Aug 2;139(30):10569-10577. doi: 10.1021/jacs.7b06007. Epub 2017 Jul 20.

PMID:
28683552
34.

Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining reveals convergent evolution.

Huang AC, Kautsar SA, Hong YJ, Medema MH, Bond AD, Tantillo DJ, Osbourn A.

Proc Natl Acad Sci U S A. 2017 Jul 18;114(29):E6005-E6014. doi: 10.1073/pnas.1705567114. Epub 2017 Jul 3.

35.

Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.

Abbasov ME, Hudson BM, Tantillo DJ, Romo D.

Chem Sci. 2017 Feb 1;8(2):1511-1524. doi: 10.1039/c6sc04273b. Epub 2016 Oct 21.

36.
37.

Synthesis of Benzodihydrofurans by Asymmetric C-H Insertion Reactions of Donor/Donor Rhodium Carbenes.

Lamb KN, Squitieri RA, Chintala SR, Kwong AJ, Balmond EI, Soldi C, Dmitrenko O, Castiñeira Reis M, Chung R, Addison JB, Fettinger JC, Hein JE, Tantillo DJ, Fox JM, Shaw JT.

Chemistry. 2017 Sep 4;23(49):11843-11855. doi: 10.1002/chem.201701630. Epub 2017 Aug 10.

PMID:
28544228
38.

Navigating Past a Fork in the Road: Carbocation-π Interactions Can Manipulate Dynamic Behavior of Reactions Facing Post-Transition-State Bifurcations.

Hare SR, Pemberton RP, Tantillo DJ.

J Am Chem Soc. 2017 Jun 7;139(22):7485-7493. doi: 10.1021/jacs.7b01042. Epub 2017 May 24.

PMID:
28504880
39.

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.

Laws SW, Moore LC, Di Maso MJ, Nguyen QNN, Tantillo DJ, Shaw JT.

Org Lett. 2017 May 19;19(10):2466-2469. doi: 10.1021/acs.orglett.7b00468. Epub 2017 May 5.

40.

Cryptic post-transition state bifurcations that reduce the efficiency of lactone-forming Rh-carbenoid C-H insertions.

Hare SR, Tantillo DJ.

Chem Sci. 2017 Feb 1;8(2):1442-1449. doi: 10.1039/c6sc03745c. Epub 2016 Oct 21.

41.

Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.

Abbasov ME, Hudson BM, Kong W, Tantillo DJ, Romo D.

Org Biomol Chem. 2017 Apr 11;15(15):3179-3183. doi: 10.1039/c6ob02738e.

42.

Importance of Inherent Substrate Reactivity in Enzyme-Promoted Carbocation Cyclization/Rearrangements.

Tantillo DJ.

Angew Chem Int Ed Engl. 2017 Aug 14;56(34):10040-10045. doi: 10.1002/anie.201702363. Epub 2017 Jun 12. Review.

PMID:
28349600
43.

Is a 1,4-Alkyl Shift Involved in the Biosynthesis of Ledol and Viridiflorol?

Hong YJ, Tantillo DJ.

J Org Chem. 2017 Apr 7;82(7):3957-3959. doi: 10.1021/acs.joc.7b00187. Epub 2017 Mar 15.

PMID:
28277661
44.

Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase.

Mafu S, Karunanithi PS, Palazzo TA, Harrod BL, Rodriguez SM, Mollhoff IN, O'Brien TE, Tong S, Fiehn O, Tantillo DJ, Bohlmann J, Zerbe P.

Proc Natl Acad Sci U S A. 2017 Jan 31;114(5):974-979. doi: 10.1073/pnas.1612901114. Epub 2017 Jan 17.

45.

Viability of dodecahedrane-forming radical polycyclizations.

Wang SC, Tantillo DJ.

Org Biomol Chem. 2017 Mar 1;15(9):1976-1979. doi: 10.1039/c6ob02300b.

PMID:
27905615
46.

The chemical biology of the persulfide (RSSH)/perthiyl (RSS·) redox couple and possible role in biological redox signaling.

Bianco CL, Chavez TA, Sosa V, Saund SS, Nguyen QNN, Tantillo DJ, Ichimura AS, Toscano JP, Fukuto JM.

Free Radic Biol Med. 2016 Dec;101:20-31. doi: 10.1016/j.freeradbiomed.2016.09.020. Epub 2016 Sep 25.

47.

Decarboxylation Facilitated by Carbocation Formation and Rearrangement during Steam Distillation of Vetiver Oil.

Wedler HB, Newman T, Tantillo DJ.

J Nat Prod. 2016 Oct 28;79(10):2744-2748. Epub 2016 Sep 22.

PMID:
27676594
48.

The Importance of Methyl Positioning and Tautomeric Equilibria for Imidazole Nucleophilicity.

Campos RB, Menezes LR, Barison A, Tantillo DJ, Orth ES.

Chemistry. 2016 Oct 17;22(43):15521-15528. doi: 10.1002/chem.201602573. Epub 2016 Sep 6.

PMID:
27595634
49.

Does Nature Know Best? Pericyclic Reactions in the Daphniphyllum Alkaloid-Forming Cation Cascade.

Tantillo DJ.

Org Lett. 2016 Sep 16;18(18):4482-4. doi: 10.1021/acs.orglett.6b01919. Epub 2016 Aug 25.

PMID:
27559932
50.

Mechanistically informed predictions of binding modes for carbocation intermediates of a sesquiterpene synthase reaction.

O'Brien TE, Bertolani SJ, Tantillo DJ, Siegel JB.

Chem Sci. 2016 Jul 1;7(7):4009-4015. doi: 10.1039/c6sc00635c. Epub 2016 Mar 21.

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