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Asymmetric Syntheses of Pectenotoxins‐4 and ‐8, Part II: Synthesis of the C20–C30 and C31–C40 Subunits and Fragment Assembly
Author(s) -
Evans David A.,
Rajapakse Hemaka A.,
Chiu Anna,
Stenkamp Dirk
Publication year - 2002
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 - 10.1002/1521-3773(20021202)41:23<4573::aid-anie4573>3.0.co;2-s
Subject(s) - chemistry , alkylation , epoxide , stereochemistry , stereoselectivity , tetrahydrofuran , bond cleavage , enantioselective synthesis , ring (chemistry) , organic chemistry , catalysis , solvent
The total syntheses of the marine macrolides pectenotoxins‐4 and ‐8 have been realized. The pectenotoxins are a new class of marine macrolides that exhibit a high level of biological activity. Key fragment couplings include a Felkin‐selective Grignard addition reaction (green), a metalated dimethylhydrazone alkylation (red), and a late‐stage olefination reaction with a β‐alkoxy sulfone (blue). The utility of the N ‐phenylamide as a carboxy surrogate and the use of the base labile tert ‐butoxydiphenylsilyl ether is also described.