Back to Search Start Over

Total Synthesis of (+)‐Sarcophytin

Authors :
Suren J. Nemat
Leonardo J. Nannini
Erick M. Carreira
Source :
Angewandte Chemie. 130:831-834
Publication Year :
2017
Publisher :
Wiley, 2017.

Abstract

A total synthesis of the cembranoid (+)-sarcophytin is presented, featuring a Diels-Alder cycloaddition of an enone as the dienophile with an ester-derived dienoate. The study highlights a peculiar geometric preference for the Z dienoate to furnish the cycloadduct. The endgame involves a reaction cascade, including lactone opening, alcohol oxidation, and ketone epimerization to complete an efficient synthesis. A salient feature of the synthesis is the resulting reassignment of the absolute configuration, which corrects the previously reported nominal structure.

Details

ISSN :
15213757 and 00448249
Volume :
130
Database :
OpenAIRE
Journal :
Angewandte Chemie
Accession number :
edsair.doi.dedup.....454fd8521fb5afb408ca740ac8230a19
Full Text :
https://doi.org/10.1002/ange.201711372