Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (4S, 5S)-4,5-Dihydroxycyclopent-2-En-1-One Isopropylidine Ketal
- 1 April 1988
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 18 (4) , 391-402
- https://doi.org/10.1080/00397918808064002
Abstract
The title compound has been synthesized in 17% yield over six steps from 2-cyclopenten-1-one. The key step is catalytic osmylation of 4-bromo-2-cyclopenten-1-one 1,4-di-O-benzyl-D-threitol ketal to produce a chromatographically separable mixture of diastereomeric diols.Keywords
This publication has 30 references indexed in Scilit:
- Determination of the absolute configuration of six-membered-ring ketones by carbon-13 NMRJournal of the American Chemical Society, 1987
- Triply convergent synthesis of (-)-prostaglandin E2Journal of the American Chemical Society, 1986
- A selective synthesis of 3-alkyl-4-halotetrahydropyrans via the titanium tetrahalide promoted cyclization of unsaturated acetalsThe Journal of Organic Chemistry, 1986
- Homochiral ketals in organic synthesis. Diastereoselective cyclopropanationJournal of the American Chemical Society, 1985
- Allylation of Aldehydes with Etherification by Dialkoxydichlorotitanium/Allyltrimethylsilane; an Asymmetric Variant of the Sakurai ReactionAngewandte Chemie International Edition in English, 1985
- A highly stereoselective route to calcitriol lactoneThe Journal of Organic Chemistry, 1985
- Unprecedented regio- and stereochemical control in the addition of organoaluminum reagents to chiral .alpha.,.beta.-unsaturated acetalsJournal of the American Chemical Society, 1984
- Practical asymmetric synthesis of aklavinoneJournal of the American Chemical Society, 1982
- Asymmetric synthesis at prochiral centers: substituted 1,3-dioxolanesThe Journal of Organic Chemistry, 1981
- Recherches dans la série des cyclitols XLIII. Sur des éthylène‐cétals de cétoses dérivés du cyclopentaneHelvetica Chimica Acta, 1972