Total Synthesis and Stereochemical Assignment of Penicitide A

  • Org Lett. 2020 Jan 17;22(2):745-749. doi: 10.1021/acs.orglett.9b04585.
Dhiman Saha  1 ,  Sandip Guchhait  1 ,  Rajib Kumar Goswami  1
Affiliations
  • 1. School of Chemical Sciences , Indian Association for the Cultivation of Science , Jadavpur, Kolkata - 700032 , India.
PMID: 31904985 DOI: 10.1021/acs.orglett.9b04585
Abstract

Stereoselective total synthesis of marine secondary metabolite penicitide A has been accomplished for the first time following a convergent approach. The salient feature of this study includes Horner-Wadsworth-Emmons (HWE) olefination, Evans methylations, Crimmins acetate aldol reaction, and cross olefin metathesis. Our synthetic study established the stereochemistry of unassigned C-10 and C-12 centers and also disclosed the absolute configurations of C-3 and C-5 stereocenters.

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