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• W2950806931 abstract "A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereoselective routes to A are described, the first employing allylation of an α-homochiral aldehyde and the second using asymmetric crotylation of an achiral aldehyde to establish the two stereogenic centers present in A. The styryl moiety of A was attached either via Stille coupling or through a Wadsworth−Emmons condensation with diethyl benzylphosphonate. The amino acid subunit B was prepared from benzyl (2S)-2-hydroxyisocaproate by connection first to N-Boc-β-alanine or its (2R)-methyl-substituted derivative and then to (2R)-N-Boc-O-methyltyrosine or its m-chloro derivative. Fusion of the A and B subunits was accomplished by initial esterification of the former with the latter, followed by macrocyclization using diphenyl phosphorazidate. In this way, cryptophycin-3, -4, and -29 were obtained along with the nonnatural cyclic depsipeptide 52. Epoxidation of cryptophycin-3 with dimethyldioxirane gave cryptophycin-1; analogous epoxidation of 52 afforded arenastatin A (cryptophycin-24)." @default.
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• W2950806931 date "1999-08-01" @default.
• W2950806931 modified "2023-10-09" @default.
• W2950806931 title "Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae" @default.
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• W2950806931 doi "https://doi.org/10.1021/jo9907585" @default.
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