Total Synthesis of (−)-Minquartynoic Acid: An Anti-Cancer, Anti-HIV Natural Product
- 22 June 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (15) , 2517-2519
- https://doi.org/10.1021/ol026145n
Abstract
The tetraacetylenic compound, (S)-minquartynoic acid (1), is synthesized in seven linear steps and 17% overall yield from commercially available azelaic acid monomethyl ester. The key step is a one-pot three-component Cadiot−Chodkiewicz reaction to construct the tetrayne unit without using either a diyne or a triyne intermediate.Keywords
This publication has 29 references indexed in Scilit:
- Cytotoxic Polyacetylenes from the Twigs of Ochanostachys amentaceaJournal of Natural Products, 2001
- Marine natural products (1999)Natural Product Reports, 2001
- Absolute Stereochemistry and Anti-HIV Activity of Minquartynoic Acid, A Polyacetylene fromOchanostachys amentacea1aNatural Product Letters, 2001
- Minquartynoic acid from Coula edulisBiochemical Systematics and Ecology, 2000
- Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculumTetrahedron: Asymmetry, 1999
- Syntheses of two enantiomers of eicos-(4E)-en-1-yn-3-ol, a bioactive component of the marine sponge Cribrochalina vasculumTetrahedron, 1999
- Stereoselective Total Synthesis of (3R,8S)-Falcarindiol, a Common Polyacetylenic Compound from UmbellifersJournal of Natural Products, 1999
- Chemoenzymatic synthesis of (S)-eicos-(4E)-en-1-yn-3-ol, the cytotoxic principle of the marine sponge, Cribrochalina vasculumTetrahedron: Asymmetry, 1998
- Isolation Of A Novel Cytotoxic Polyacetylene From A Traditional Anthelmintic Medicinal Plant, Minquartia guianensisJournal of Natural Products, 1989
- Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) estersJournal of the American Chemical Society, 1973