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First Total Synthesis of the Proposed Structures of Orisuaveolines A and B
Author(s) -
Zhang Jie,
Da Shijun,
Feng Xiaolin,
Chen Xiaoyi,
Jiang Jianhui,
Li Ying
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200986
Subject(s) - chemistry , total synthesis , condensation , combinatorial chemistry , lactam , condensation reaction , key (lock) , stereochemistry , organic chemistry , catalysis , ecology , physics , biology , thermodynamics
First total synthesis of the proposed structures of β ‐indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet‐Spengler reaction to build a six‐member lactam which further transformed into target molecular by a one‐pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient manner from inexpensive, commercially available starting materials. The structures of our synthesized products were confirmed by 2D‐NMR experiments.