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Synlett 1994; 1994(6): 437-438
DOI: 10.1055/s-1994-22880
DOI: 10.1055/s-1994-22880
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
A Convenient Synthesis of the Toxicophoric Furo[2,3-b]benzofuran Fragment Present in Aflatoxin M1
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Publikationsverlauf
Publikationsdatum:
18. September 2002 (online)
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A one-pot procedure involving four reaction steps (enolate formation, epoxidation, epoxide opening and deprotection), constitutes the key process for obtaining the hydroxyfuro[2,3-b]benzofuran moiety present in aflatoxin M1. The above sequential reactions led to the generation of the benzopyran aldehyde 8. As expected, this aldehyde underwent equilibration in solution giving rise to the epimeric mixture of dihydroxyfuro[2,3-b]benzofurans 9 as major components. This epimeric mixture was easily converted into the toxicophoric aflatoxin M1 fragment 10.