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J Org Chem. 2018 Jul 6;83(13):6893-6906. doi: 10.1021/acs.joc.7b02915. Epub 2018 Mar 15.

Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System.

Author information

1
State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
2
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology , Shenzhen Graduate School of Peking University , Shenzhen 518055 , China.

Abstract

The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson-Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.

PMID:
29508610
DOI:
10.1021/acs.joc.7b02915

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