73541-95-4Relevant articles and documents
Preparation of lactones
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, (2008/06/13)
7-Substituted lower alkyl hept-6-enoates and 4-hydroxytetrahydropyran-2-ones bearing 6-olefinic substituents (e.g.,) ethyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoates are prepared by a multi-step process. The process involves 3-protected-lower alkyl 3,5
A Highly Convergent Total Synthesis of (+)-Compactin
Keck, Gary E.,Kachensky, David F.
, p. 2487 - 2493 (2007/10/02)
An intramolecular Diels-Alder approach to the construction of (+)-compactin is described.Alkylation of the lithium enolate of (acetylmethylene)triphenylphosphorane with the tosylate of allenic alcohol 15 affords phosphorane 16, which condenses with aldehyde 6 (prepared from tri-O-acetyl-D-glucal) to afford enone 3.Intramolecular Diels-Alder reaction, reduction with lithium tri-sec-butylborohydride, and acylation with (S)-(+)-2-methylbutyric anhydride yields a chromatographically separable mixture of diastereomers; conversion to compactin was accomplished by acid hydrolysis followed by oxidation.
Synthetic and biological studies of compactin and related compounds. 2 Synthesis of the lactone moiety of compactin
Rosen,Taschner,Heathcock
, p. 3994 - 4003 (2007/10/02)
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