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 SmI(2)-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.
Nishikawa
Keisuke
K
Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan.
Nakahara
Hiroshi
H
Shirokura
Yousuke
Y
Nogata
Yasuyuki
Y
Yoshimura
Erina
E
Umezawa
Taiki
T
Okino
Tatsufumi
T
Matsuda
Fuyuhiko
F
D000438:Alcohols / Q000737:chemistry; D000818:Animals; D057219:Biofouling / Q000517:prevention & control; D003486:Cyanides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013237:Stereoisomerism; D001468:Thoracica / Q000187:drug effects
C480379:10-isocyano-4-cadinene; D000438:Alcohols; D003486:Cyanides; D009281:Naphthalenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes