Total syntheses of natural (+)-(4R,6R)-4-hydroxy-6-pentylvalerolactone and of (–)-(6R)-massoialactone
Authors:
- Frank BennettFBFrank Bennett
- David W. KnightDKDavid W. Knight
- Garry FentonGFGarry Fenton
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1543-1547
Abstract
An asymmetric total synthesis and hence a confirmation of the absolute configuration of naturally occurring (+)-(4R,6R)-4-hydroxy-6-pentylvalerolactone 10, a metabolite of Cephalosporium recifei, is described, starting from the yeast reduction product methyl (3R)-3-hydroxyhex-5-enoate 5. The key step is a highly trans-selective kinetic iodolactonization of the unsaturated acid 16e. Dehydration of the lactone 10 leads to natural (–)-(6R)-massoialactone 11.Keywords
This publication has 24 references indexed in Scilit:
- Synthesis of (+)-dihydromevinolin by selective reduction of mevinolinThe Journal of Organic Chemistry, 1989
- Synthesis of optically active mevinic acid subunits via acetal initiated/vinylsilane terminated polyene cyclizationsTetrahedron Letters, 1989
- Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special TiCl3/C8K mixture for dicarbonyl couplingJournal of the American Chemical Society, 1988
- An Alternative Approach to Mevinic Acid Analogues from Methyl (3)-3-Hydroxy-5-Hexenoate and an Extension to Rational Syntheses of (+)-(6)-Goniothalamin and its Non-natural (-)-(6)-EnantiomerTetrahedron Letters, 1988
- 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 3. 7-(3,5-Disubstituted-[1,1'-biphenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivativesJournal of Medicinal Chemistry, 1986
- 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 2. Structural modification of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivativesJournal of Medicinal Chemistry, 1986
- The synthesis of mevinic acidsTetrahedron, 1986
- Preparation of ethyl 5(s),6-epoxy-3(r)-(methoxymethoxy)hexanoate: a key chiral intermediate for mevinolin and compactin.Tetrahedron Letters, 1985
- Compactin (ML-236B) and related compounds as potential cholesterol-lowering agents that inhibit HMG-CoA reductaseJournal of Medicinal Chemistry, 1985
- 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. I. Structural modification of 5-substituted 3,5-dihydroxypentanoic acids and their lactone derivativesJournal of Medicinal Chemistry, 1985