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An Efficient Approach to the Total Synthesis of Ammosamide B
Author(s) -
Yang ShengWei,
Wang ChunMeng,
Tang KaiXiang,
Wang JinXin,
Sun LiPing
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501560
Subject(s) - chemistry , yield (engineering) , total synthesis , stereochemistry , intermolecular force , combinatorial chemistry , organic chemistry , molecule , materials science , metallurgy
A new approach for the total synthesis of ammosamide B was realized. The strategy is based on an intermolecular Pd‐catalyzed N ‐arylation of 4‐chloro‐1‐methylindoline‐2,3‐dione ( 2 ), which enables construction of the key pyrroloquinoline skeleton precursor 6 within three steps in an overall yield of 80 %. The ammosamide B total synthesis is achieved in 12 simple transformations by starting from a commercially available starting material and proceeds with an overall yield of 23 %. Additionally, key precursor 6 represents an important intermediate in the synthesis of other pyrroloquinoline‐containing natural products.