A synthetic study on antiviral and antioxidative chromene derivative.

Abstract:

:An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be synthesized for evaluation of their biological activity and mechanistic study. The total synthesis of 1, started from geranyl acetate and protected 2-bromo-6-methylhydroquinone, was executed with Sharpless asymmetric dihydroxylation for introduction of the terminal diol system and base-catalyzed sigmatropic rearrangement for construction of the chromene skeleton as the crucial steps. The stereochemistry at C-11' was reconfirmed by this synthesis.

authors

Mori J,Iwashima M,Takeuchi M,Saito H

doi

10.1248/cpb.54.391

subject

Has Abstract

pub_date

2006-03-01 00:00:00

pages

391-6

issue

3

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/54.391

journal_volume

54

pub_type

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