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Synlett 1993; 1993(8): 555-556
DOI: 10.1055/s-1993-22526
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An Efficient Formal Synthesis of Aflatoxin B2 by Use of the Kikuchi Rearrangement Reaction

Masato Koreeda* , Lisa A. Dixon, Jeffrey D. Hsi
  • *Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055, USA
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Publication Date:
19 March 2002 (online)

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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.

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