86030-92-4Relevant academic research and scientific papers
Preparation of lactones
-
, (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
4-trisubstituted silyl protected hydroxy-6-oxo-tetrahydropyran-2-yl-aldehyde intermediates
-
, (2008/06/13)
6-trans-indol-2-yl-ethenyl)-4-hydroxy-tetrahydro-2H-pyran-2-ones of formula I are obtained by a multi-step reaction involving the procedure: STR1 wherein p1 is trisubstituted silyl protective group, and Z is a 2-indolyl radical which may be bea
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.
Convergent, Enantiospecific Total Synthesis of the Hypocholesterolemic Agent (+)-Compactin
Grieco, Paul A.,Lis, Randall,Zelle, Robert E.,Finn, John
, p. 5908 - 5919 (2007/10/02)
A convergent, enantiospecific total synthesis of (+)-compactin (1) is described.The strategy for the construction of the (+)-1 centers around a Diels-Alder reaction between chiral dienophile 23 and chiral diene 62 which provides in a single operation access to allylic sulfide 85 possessing the desired configuration at C(8'), C(8a'), and C(1').Dienophile 23 is made readily available by resolution of the known racemic β-nitro acid 66.The synthesis of diene 62 commences with the known epoxide 7 derived from tri-O-acetyl-D-glucal.Diels-Alder adduct 85 is transformed into allylic alcohol 87 which sets the stage for incorporation of the C(2') methyl group.Elaboration of the hexalol portion of compactin with liberation of the C(8') hydroxyl group is achieved via a Grob-like fragmentation on alcohol 95.Acylation 94, subsequent adjustment of the oxidation state at C(1), and demethylation give way to (+)-compactin.
MEVINIC ACIDS AND ANALOGUES: PREPARATION OF A KEY CHIRAL INTERMEDIATE
Yang, Yuh-Lin,Falck, J.R.
, p. 4305 - 4308 (2007/10/02)
The preparation of methyl 3-O-tert-butyldiphenylsilyl-2,4-dideoxy-β-D-erytrohexopyranoside, a key chiral intermediate for mevinic acids, and its elaboration into four mevinate analogues are described.
