The new method for introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one and its application to chiral Wieland-Miescher type compound synthesis.

Abstract:

:The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initially formed one. Two diastereomeric Wieland-Miescher type compounds, having the allyl group at the angular position, were synthesized as optically pure forms.

authors

Hiroya K,Takahashi T,Shimomae K,Sakamoto T

doi

10.1248/cpb.53.207

subject

Has Abstract

pub_date

2005-02-01 00:00:00

pages

207-13

issue

2

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/53.207

journal_volume

53

pub_type

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