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A Convergent Approach to (−)‐Callystatin A Based on Local Symmetry
Author(s) -
Candy Mathieu,
Tomas Loïc,
Parat Sabrina,
Heran Virginie,
Bienaymé Hugues,
Pons JeanMarc,
Bressy Cyril
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202701
Subject(s) - stereocenter , stille reaction , local symmetry , symmetry (geometry) , natural product , product (mathematics) , chemistry , computer science , stereochemistry , catalysis , mathematics , physics , enantioselective synthesis , organic chemistry , quantum mechanics , geometry
The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (−)‐callystatin A was developed assembling three fragments through Julia–Kocienski olefination and Stille cross‐coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme).