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An Approach to the Carbon Backbone of Bielschowskysin, Part 1: Photocyclization Strategy
Author(s) -
Himmelbauer Martin,
Farcet JeanBaptiste,
Gagnepain Julien,
Mulzer Johann
Publication year - 2013
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.201300869
Subject(s) - enantiopure drug , chemistry , cyclobutane , diterpene , cope rearrangement , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , ring (chemistry)
Several macrocyclization reaction attempts of highly advanced precursors toward a total synthesis of marine diterpene bielschowskysin are disclosed. Biomimetic [2+2]‐photocyclization reactions were applied to construct the cyclobutane core in these intermediates, which could be accessed along scalable high‐yielding reaction sequences from cheap enantiopure starting‐materials.