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Asymmetric Syntheses of Pectenotoxins‐4 and ‐8, Part I: Synthesis of the C1–C19 Subunit
Author(s) -
Evans David A.,
Rajapakse Hemaka A.,
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<4569::aid-anie4569>3.0.co;2-v
Subject(s) - alkylation , chemistry , sulfone , ether , stereochemistry , organic chemistry , catalysis
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.