Issue 89, 2015

Total synthesis of (−)-depyranoversicolamide B

Abstract

Starting from easily prepared (R)-C3-isoprenylated pyrroloindoline, the C3-isoprenylated indolyl diketopiperazine is prepared by an efficient reductive opening of the pyrrolo ring, and undergoes biomimetic Diels–Alder reaction to generate an anti-adduct as a sole stereoisomer. Oxidation of the indoline moiety to oxindole completes the synthesis of (−)-depyranoversicolamide B.

Graphical abstract: Total synthesis of (−)-depyranoversicolamide B

Supplementary files

Article information

Article type
Communication
Submitted
15 Jul 2015
Accepted
10 Sep 2015
First published
10 Sep 2015

Chem. Commun., 2015,51, 16143-16146

Total synthesis of (−)-depyranoversicolamide B

W. Qin, T. Xiao, D. Zhang, L. Deng, Y. Wang and Y. Qin, Chem. Commun., 2015, 51, 16143 DOI: 10.1039/C5CC05877E

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