Total synthesis of avenaol.

ABSTRACT: Avenaol, isolated from the allelopathic plant black oat, was the first C₂₀ germination stimulant related to strigolactones. Structurally, it consisted of a bicyclo[4.1.0]heptanone skeleton containing a cyclopropane ring bearing three main chains projecting in the same direction (i.e. all-cis-substituted cyclopropane). Herein, we report the total synthesis of avenaol using a robust strategy involving the formation of an all-cis-substituted cyclopropane via an alkylidenecyclopropane. The key factors in the success of this total synthesis include the Rh-catalysed intramolecular cyclopropanation of an allene, an Ir-catalysed stereoselective double-bond isomerisation, and the differentiation of two hydroxymethyl groups via the regioselective formation and oxidation of a tetrahydropyr

SUBMITTER: Yasui M 

PROVIDER: S-EPMC5610312 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature