Journal
TETRAHEDRON
Volume 67, Issue 35, Pages 6730-6745Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.006
Keywords
(+)-Spiculoic acid A; (+)-Zyggomphic acid; Marine natural product; Cytotoxicity; Intramolecular reaction Diels-Alder reaction
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [18032069]
- Grants-in-Aid for Scientific Research [18032069] Funding Source: KAKEN
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The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described. (C) 2011 Elsevier Ltd. All rights reserved.
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