| A General Access to Taiwaniaquinoids Based on a Hypothetical Abietane C7-C8 Cleavage Biogenetic Pathway. | |
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MedLine Citation:
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PMID: 22118292 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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A new strategy for synthesizing taiwaniaquinoids, a group of terpenoids with an unusual rearranged 5(6->7) or 6-nor-5(6->7)abeo-abietane skeleton, which exhibit promising biological activities, is reported. The procedure, based on the cleavage of the C7-C8 double bond of abietane diterpenes, is the only one yet reported for synthesizing C20 taiwaniaquinoids bearing a carbon function on the cyclopentane B ring; it is also applicable to the synthesis of the wide variety of existing taiwaniaquinoids. Utilizing this, (-)-taiwaniaquinone A, F, G and H, (-)-taiwaniaquinol B and (-)-dichroanone have been synthesized fron (+)-abietic acid. The versatility of this strategy allows us to propose the abietane C7-C8 cleavage as a possible biosynthetic pathway to this type of rearranged diterpenes; this proposal seems to be supported by phytochemical evidences. |
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Authors:
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Ruben Tapia; Juan J Guardia; Esteban Alvarez; Ali Haidour; Jose Miguel Ramos; Ramon Alvarez-Manzaneda; Rachid Chahboun; Enrique Alvarez-Manzaneda |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-11-25 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Nov |
Date Detail:
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Created Date: 2011-11-28 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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