Total Synthesis of 10-Isocyano-4-cadinene and Determination of Its Absolute Configuration

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels−Alder reaction and a SmI2-indu...

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Bibliographic Details
Published in:Organic letters 2010-03, Vol.12 (5), p.904-907
Main Authors: Nishikawa, Keisuke, Nakahara, Hiroshi, Shirokura, Yousuke, Nogata, Yasuyuki, Yoshimura, Erina, Umezawa, Taiki, Okino, Tatsufumi, Matsuda, Fuyuhiko
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Animals
Biofouling - prevention & control
Cyanides - chemical synthesis
Cyanides - chemistry
Cyanides - pharmacology
Magnetic Resonance Spectroscopy
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Naphthalenes - pharmacology
Sesquiterpenes
Stereoisomerism
Thoracica - drug effects
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Summary:The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels−Alder reaction and a SmI2-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano-4-cadinene were also evaluated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9027336