ビンドリンおよび関連アルカロイド類の全合成

概要

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A concise 11-step total synthesis of (−)- and ent-(+)-vindoline is detailed based on a unique tandem intramolecular [4+2]/[3+2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which three rings and four C-C bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As a key elements of the scope and stereochemical features of the reaction were defined, a series of related natural products of increasing complexity were also prepared by total synthesis including both enantiomers of vindorosine, minovine, 4-desacetoxyvindoline, 4-desacetoxy-5-desethylvindoline and 4-deaacetoxyvindorosine as well as N-methylaspidospermidine.