Biomimetic Synthesis of (±)-Merochlorin B

R Meier, S Strych, D Trauner

Index: Meier, Robin; Strych, Sebastian; Trauner, Dirk Organic Letters, 2014 , vol. 16, # 10 p. 2634 - 2637

Full Text: HTML

Citation Number: 10

Abstract

A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (D o M), a selective demethylation, an ortho-allylation, and an oxidative [3+ 2]-cycloaddition mediated by an iodine (III) reagent.