Synthetic study of diversifolin: the construction of 11-oxabicyclo[6.2.1]undec-3-ene core using ring-closing metathesis.
Stereoselective synthesis of a potential intermediate bearing 11-oxabicyclo[6.2.1]undec-3-ene core, a common scaffold of biologically active germacrane-type sesquiterpenes, has been achieved. Synthetic features involve formal 1,3-asymmetric induction, unusual ring-closing metathesis constructing a 10-membered carbocycle system, and unique lactone transposition.
Nakamura
Tomoaki
T
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Oshida
Motoko
M
Nomura
Tomoko
T
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D007783:Lactones; D012717:Sesquiterpenes; C115944:diversifolin