Total synthesis of (+/-)-clavubicyclone.
[reaction: see text] The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation.
Ito
Hisanaka
H
School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. itohisa@las.toyaku.ac.jp
Takeguchi
Shunta
S
Kawagishi
Takahiro
T
Iguchi
Kazuo
K
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D007564:Japan; D015394:Molecular Structure; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011453:Prostaglandins; C463700:clavubicyclone