AN EFFICIENT FORMAL SYNTHESIS OF AFLATOXIN-B(2) BY USE OF THE KIKUCHIREARRANGEMENT REACTION

Authors
KOREEDA M DIXON LA HSI JD
Citation
M. Koreeda et al., AN EFFICIENT FORMAL SYNTHESIS OF AFLATOXIN-B(2) BY USE OF THE KIKUCHIREARRANGEMENT REACTION, Synlett, (8), 1993, pp. 555-556
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1993
Pages
555 - 556
Database
ISI
SICI code
0936-5214(1993):8<555:AEFSOA>2.0.ZU;2-5
Abstract
A five-step, highly efficient synthesis of tetrahydrofurobenzofuran 2, the pivotal intermediate in the synthesis of aflatoxin B2, has been a chieved in 24% (40% on the basis of the recovered aldehyde for the Wit tig conversion of 5a to 4a) overall yield from 5a. The key chain-branc hing step that provided the tetrahydobisfuran carbon framework has bee n achieved by use of the Kikuchi rearrangement reaction, i.e., treatme nt with I2, Ag2O, dioxane/H2O of the styrene system 4b.