Enantioselective Synthesis of Eucomols Using Sharpless Catalytic Asymmetric Dihydroxylation
Year: 1997
Type: article
Abstract: A novel synthetic method was developed for eucomols, (S)-3hydroxyhomoisoflavanones.Addition of aryllithium to aldehyde ((9-9) obtained by asymmetric dihydroxylation of 4, followed by the formation of cyclic ether, gave eucomols, (8-3-hydroxyhomoisoflavanones (la-e).As a small family of natural products, homoisoflavanones have been isolated from several genera in Liliaceae'and Caesalpinoideae (Leguminosae).'According to their structural features, these can be classified into three types which are eucomin (3-benzylidenechroman-4-one), dihydroeucomin (3-benzylchroman-4-one) and eucomol (3-hydroxy-3-benzylchroman-4-one).'"Several eucomols and the related compounds such as (R)and (8-5,7-0-dimethyleucomol," (R)-0-trimethylsappanone B and (+)-0-trimethylbrazilin,d and (8-8-benzyloxy-0-tribenzylsappanone B and (-)-haematoxylin5 have various important biological properties.These all compounds have one chiral center at C(3) position.Because their biological activities are dependent upon the absolute configuration,'" the biologically active eucomols should be obtained in chiral forms.The asymmetric synthesis of the eucomols, (R)-or ( 9 3 -
Source: Heterocycles
DOI: 10.3987/com-97-s24
Institutions: Seoul National University, The University of Tokyo
Language: English
Subfield: Pharmacology
Field: Medicine
Domain: Health Sciences
Open Access status: diamond
OpenAlex ID: W2951335293