Issue 89, 2015
From the journal:

Chemical Communications

Total synthesis of (−)-depyranoversicolamide B†

Wen-Fang Qin,a   T. Xiao,a   D. Zhang,*b   Lin-Feng Deng,b   Y. Wangb  and  Y. Qin*b  

* Corresponding authors

a The Innovative Drug Research Centre, and School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 401331, P. R. China

b Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China
E-mail: yongqin@scu.edu.cn, danzhang@scu.edu.cn

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

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Article information

DOI
https://doi.org/10.1039/C5CC05877E
Article type
Communication
Submitted
15 Jul 2015
Accepted
10 Sep 2015
First published
10 Sep 2015

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

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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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