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Synthesis 2006(1): 166-181
DOI: 10.1055/s-2005-921760
DOI: 10.1055/s-2005-921760
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of Terpenoids Isolated from Caulerpale Algae and Their Inhibition of Tubulin Assembly
Further Information
Received
28 September 2005
Publication Date:
16 December 2005 (online)
Publication History
Publication Date:
16 December 2005 (online)
Abstract
Total synthesis of four analogue terpenoids isolated from Caulerpa taxifolia was achieved in good yield with a total control of each double bond. Biological tests to compare the activities of in vitro tubulin polymerisation between the natural caulerpenyne and the synthetic caulerpenyne and its derivatives were also performed.
Key words
total synthesis - caulerpenyne - dihydrorhipocephalin - furocaulerpin - terpenoids - microtubule polymerisation
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References
Compound 24 was obtained as a separable mixture with the isomer resulting from an acylotropy of the primary acetate function. Using tetrabutylammonium fluoride as a deprotecting agent, acylotropy reaction largely occurred, providing a mixture of mono-, di- and triacetate isomers of 24.
37The optical signs of iso-caulerpenyne, dihydrorhipocephalin and iso-dihydrorhipocephalin are those observed by the on-line circular dichroism at 220 nm of the products in the solvent used for the chromatographic separation.