Issue 1, 2015

Synthesis of fully functionalized aglycone of lycoperdinoside A and B

Abstract

This article reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille–Migita cross coupling between E-vinyl iodide 6 and E-vinyl stannane 23 established the highly substituted E,E-diene unit present in lycoperdinoside A and B. The other two Z-olefins present in the molecule were introduced by means of cis-selective Horner–Wadsworth–Emmons reaction with Still–Gennari phosphonate. Evans syn- and anti-aldol reactions were utilized to fix six of the seven stereo centres present in the aglycone.

Graphical abstract: Synthesis of fully functionalized aglycone of lycoperdinoside A and B

Supplementary files

Article information

Article type
Paper
Submitted
11 Aug 2014
Accepted
30 Sep 2014
First published
01 Oct 2014

Org. Biomol. Chem., 2015,13, 115-124

Synthesis of fully functionalized aglycone of lycoperdinoside A and B

B. Chandrasekhar, S. Athe, P. P. Reddy and S. Ghosh, Org. Biomol. Chem., 2015, 13, 115 DOI: 10.1039/C4OB01716A

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