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Total Synthesis of (±)‐Photodeoxytridachione through a Lewis Acid Catalyzed Cyclization
Author(s) -
Miller Aubry K.,
Trauner Dirk
Publication year - 2003
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.200390158
Subject(s) - lewis acids and bases , catalysis , total synthesis , chemistry , stereochemistry , concerted reaction , mechanism (biology) , organic chemistry , philosophy , epistemology
Concerted or stepwise: The concise total synthesis of the molluscan polypropionate photodeoxytridachione ( 3 ) features a Lewis acid catalyzed cyclization of tetraenoic ester 1 to form bicylo[3.1.0]hexene 2 as a key step. The stereochemistry of the cyclization can be rationalized in terms of a stepwise or a concerted mechanism.