title: Total Synthesis of (-)-Maytansinol.
abstract: A total synthesis of maytansinol (1) was achieved, in a convergent way, using (3S,6S,7S)-aldehyde 4 and (S)-p-tolyl sulfoxide 3 as fragments. When the anion of 3 was condensed with aldehyde 4, some induction at C(10) was observed (60% de), giving the C(1)-N(19)-open-chain compound 7, after thermal elimination of sulfinate. Pure E/E stereochemistry of the 11,13-diene was obtained. Selective modifications of the functionalities permitted macrocyclization and further elaboration to maytansinol.
authors.affiliation: CNRS, Institut de Chimie des Substances Naturelles, 91198 Gif-sur-Yvette, France.
authors.forename: Michel
authors.initials: M
authors.lastname: Bénéchie
authors.forename: Françoise
authors.initials: F
authors.lastname: Khuong-Huu