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Rapid Syntheses of (−)‐FR901483 and (+)‐TAN1251C Enabled by Complexity‐Generating Photocatalytic Olefin Hydroaminoalkylation
Author(s) -
Reich Dominik,
Trowbridge Aaron,
Gaunt Matthew J.
Publication year - 2020
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.201912010
Subject(s) - photocatalysis , olefin fiber , combinatorial chemistry , process (computing) , chemistry , nanotechnology , biochemical engineering , computer science , organic chemistry , materials science , catalysis , engineering , operating system
We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (−)‐FR901483 ( 1 ) and (+)‐TAN1251C ( 2 ). A divergent synthetic strategy provides access to both natural products through a pivotal spirolactam intermediate ( 3 ), which can be accessed on a gram‐scale. A photocatalytic olefin hydroaminoalkylation brings together three readily available building blocks and forges the majority of the carbon framework present in 1 and 2 in a single operation, leading to concise total syntheses. The complexity‐generating photocatalytic process also provides direct access to novel non‐racemic spirolactam scaffolds that are likely to be of interest to early‐stage drug discovery programs.