Total synthesis of ceratopicanol through tandem cycloaddition reaction of a linear substrate.
Total synthesis of ceratopicanol (1) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary carbon centers and showed an unusual diastereoselectivity.
Department of Chemistry, KAIST, 373-1 Gusung Dong, Yuseong, Daejeon, 305-701, Korea.
Sang-Shin
SS
Lee
Won-Yeob
WY
Kim
Hee-Yoon
HY
Lee
D001391:Azo Compounds / Q000737:chemistry; D061565:Cycloaddition Reaction; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001391:Azo Compounds; D011083:Polycyclic Compounds; C464976:ceratopicanol; C522820:trimethylenemethane; D008697:Methane