An Efficient Formal Synthesis of Aflatoxin B2 by Use of the Kikuchi Rearrangement Reaction

Abstract

A five-step, highly efficient synthesis of tetrahydrofurobenaofuran 2, the pivotal intermediate in the synthesis of aflatoxin B2, has been achieved in 24% (40% on the basis of the recovered aldehyde for the Wittig conversion of 5a to 4a) overall yield from 5a. The key chain-branching step that provided the tetrahydrobisfuran carbon framework has been achieved by use of the Kikuchi rearrangement reaction, i.e., treatment with I2, Ag2O, dioxane/H2O of the styrene system 4b.