Stereoselective Syntheses of Dihydroxerulin and Xerulinic Acid, Anti‐Hypocholesterolemic Dyes from the Fungus  Xerula melanotricha | Zendy

Sorg Achim | Zendy; Siegel Konrad | Zendy; Brückner Reinhard | Zendy

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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.

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