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Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(-)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(-)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol.

Michael JP, Accone C, de Koning CB, van der Westhuyzen CW.

Beilstein J Org Chem. 2008 Jan 18;4:5.PMID: 18205934 [PubMed - in process]Related articlesFree article

Studies towards the enantioselective synthesis of 5,6,8-trisubstituted amphibian indolizidine alkaloids via enaminone intermediates.

Michael JP, de Koning CB, van der Westhuyzen CW.

Org Biomol Chem. 2005 Mar 7;3(5):836-47. Epub 2005 Jan 31.PMID: 15731870 [PubMed - indexed for MEDLINE]Related articlesFree article

A convenient new route to piperidines, pyrrolizidines, indolizidines, and quinolizidines by cyclization of acetylenic sulfones with beta and gamma-chloroamines. Enantioselective total synthesis of indolizidines (-)-167B, (-)-209D, (-)-209B, and (-)-207A.

Back TG, Nakajima K.

J Org Chem. 2000 Jul 28;65(15):4543-52.PMID: 10959857 [PubMed - indexed for MEDLINE]Related articles

Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.

Amat M, Llor N, Hidalgo J, Escolano C, Bosch J.

J Org Chem. 2003 Mar 7;68(5):1919-28.PMID: 12608811 [PubMed - indexed for MEDLINE]Related articles

A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids.

Remuson R.

Beilstein J Org Chem. 2007 Oct 2;3:32.PMID: 17910752 [PubMed - in process]Related articlesFree article

A stereospecific synthesis of (+/-)-5,8-disubstituted indolizidines and (+/-)-1,4-disubstituted quinolizidines found in poison frog skins.

Michel P, Rassat A, Daly JW, Spande TF.

J Org Chem. 2000 Dec 29;65(26):8908-18.PMID: 11149832 [PubMed - indexed for MEDLINE]Related articles

A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction.

Barluenga J, Mateos C, Aznar F, Valdés C.

Org Lett. 2002 May 30;4(11):1971-4.PMID: 12027660 [PubMed - indexed for MEDLINE]Related articles

Flexible synthetic routes to poison-frog alkaloids of the 5,8-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A, (-)-205A, and (-)-219F.

Toyooka N, Zhou D, Nemoto H, Garraffo HM, Spande TF, Daly JW.

Beilstein J Org Chem. 2007 Sep 28;3:29.PMID: 17903239 [PubMed - in process]Related articlesFree article

A short route toward chiral, polyhydroxylated indolizidines and quinolizidines.

Verhelst SH, Paez Martinez B, Timmer MS, Lodder G, van der Marel GA, Overkleeft HS, van Boom JH.

J Org Chem. 2003 Dec 12;68(25):9598-603.PMID: 14656083 [PubMed - indexed for MEDLINE]Related articles

[Synthesis and its application to the synthesis of biologically active natural products of new and versatile chiral building blocks]

Toyooka N.

Yakugaku Zasshi. 2001 Jul;121(7):467-79. Review. Japanese. PMID: 11494594 [PubMed - indexed for MEDLINE]Related articlesFree article

Development of versatile cis- and trans-dicarbon-substituted chiral cyclopropane units: synthesis of (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and their enantiomers as conformationally restricted analogues of histamine.

Kazuta Y, Matsuda A, Shuto S.

J Org Chem. 2002 Mar 8;67(5):1669-77.PMID: 11871901 [PubMed - indexed for MEDLINE]Related articles

Enantiocontrolled synthesis of 2,3,6-trisubstituted piperidines using (eta(3)-dihydropyridinyl)molybdenum complexes as chiral scaffolds. Total synthesis of (-)-indolizidine 209B.

Shu C, Alcudia A, Yin J, Liebeskind LS.

J Am Chem Soc. 2001 Dec 19;123(50):12477-87.PMID: 11741410 [PubMed - indexed for MEDLINE]Related articles

Tuning the acceptors in catalyzed cyclizations initiated by allenes. Silylstannylation/cyclization of allene-aldehydes for synthesis of polyalkylated indolizidines including 223A congeners.

Kumareswaran R, Gallucci J, Rajanbabu TV.

J Org Chem. 2004 Dec 24;69(26):9151-8.PMID: 15609949 [PubMed]Related articles

Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone.

Davies SG, Hughes DG, Nicholson RL, Smith AD, Wright AJ.

Org Biomol Chem. 2004 May 21;2(10):1549-53. Epub 2004 Apr 27.PMID: 15136813 [PubMed - indexed for MEDLINE]Related articlesFree article

Facile transformation of 2-azetidinones to 2-piperidones: application to the synthesis of the indolizidine skeleton and (8S,8aS)-perhydro-8-indolizinol.

Lee HK, Chun JS, Pak CS.

J Org Chem. 2003 Mar 21;68(6):2471-4.PMID: 12636419 [PubMed]Related articles

Alkaloids in Madagascan frogs (Mantella): pumiliotoxins, indolizidines, quinolizidines, and pyrrolizidines.

Garraffo HM, Caceres J, Daly JW, Spande TF, Andriamaharavo NR, Andriantsiferana M.

J Nat Prod. 1993 Jul;56(7):1016-38.PMID: 8377013 [PubMed - indexed for MEDLINE]Related articles

Total synthesis of the indolizidine alkaloid tashiromine.

Marsden SP, McElhinney AD.

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Nonracemic bicyclic lactam lactones via regio- and cis-diastereocontrolled C-H insertion. Asymmetric synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

Wee AG, Fan GJ, Bayirinoba HM.

J Org Chem. 2009 Nov 6;74(21):8261-71.PMID: 19807135 [PubMed - in process]Related articles

Indolizidine and quinolizidine alkaloids.

Michael JP.

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Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines.

Dave R, Sasaki NA.

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