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Reaction of Donor‐Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)‐Strychnine and the Total Synthesis of (±)‐Akuammicine
Author(s) -
Feng LiangWen,
Ren Hai,
Xiong Hu,
Wang Pan,
Wang Lijia,
Tang Yong
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611734
Subject(s) - cyclobutanes , total synthesis , strychnine , chemistry , stereochemistry , toxicology , organic chemistry , biology , catalysis , biochemistry , cycloaddition
A ligand‐promoted catalytic [4+2] annulation reaction using indole derivatives and donor‐acceptor (D‐A) cyclobutanes is reported, thus providing an efficient and atom‐economical access to versatile cyclohexa‐fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94 % ee. This novel synthetic method is applied as a general protocol for the total synthesis of (±)‐akuammicine and the formal total synthesis of (±)‐strychnine from the same common‐core scaffold.