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Stereoselective Syntheses of Dihydroxerulin and Xerulinic Acid, Anti‐Hypocholesterolemic Dyes from the Fungus Xerula melanotricha
Author(s) -
Sorg Achim,
Siegel Konrad,
Brückner Reinhard
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400913
Subject(s) - stereoselectivity , levulinic acid , chemistry , alcohol , stereochemistry , allyl alcohol , biosynthesis , fungus , cis–trans isomerism , organic chemistry , catalysis , enzyme , biology , botany
The title compounds 2 and 3 , which are inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans , cis , trans ‐ 35 or trans , trans , trans ‐ 35 [each accessible from 3‐(tributylstannyl)allyl alcohol ( 17 ) in four steps], giving γ‐alkylidenebutenolide trans , trans , trans ‐ 32 . This compound was coupled with iododiyne 42 or the bromoenediynoate 44 leading to dihydroxerulin ( 2 ) and to the (trimethylsilylethyl)ester 45 of xerulinic acid, respectively. Deprotection of the latter provided totally synthetic xerulinic acid ( 3 ) for the first time.