Synthesis 2022; 54(09): 2225-2232
DOI: 10.1055/s-0041-1737805
paper

First Total Syntheses of (±)-Callyspongidic Acids and 2-epi-(±)-Callyspongidic Acids

Sayani Das
,
Anju Bala
,
Kapil Sharma
,
This work was supported by the Science and Engineering Research Board, SERB (DST) (file no YSS/2015/000660).


Abstract

The first total syntheses of (±)-callyspongidic acids and 2-epi-(±)-callyspongidic acids were achieved in high overall yield from epoxy ester derived from commercially available l-(+)-tartaric acid. The key features of these syntheses are the stereoselective opening of epoxide with organocuprates and the chemoselective addition of Grignard reagent to ketone in the presence of ester. The synthetic route reported here is operationally simple, very short and amenable for the synthesis of several analogues of this class.

Supporting Information



Publication History

Received: 15 November 2021

Accepted after revision: 13 December 2021

Article published online:
01 February 2022

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