Total synthesis of cyathin A3 and cyathin B2
Abstract
The total synthesis of cyathin B2 and cyathin A3 was achieved. The cyathane diterpenoids typically contain a 5,6,7-tricyclic core with the 6,7-trans ring junction. A synthetic challenge lies in the challenging diastereocontrol of the trans ring junction stereochemistry. A Prins-type reaction of a cycloalkenylcyclopropanol silyl ether with an oxocarbenium ion intermediate afforded the spirocyclobutanone adduct. This suitably substituted spirocyclobutanone provided a unique approach to the syntheses of the cyathane diterpenoids in conjunction with a ring closing metathesis reaction.
Recommended Citation
Keunho Kim,
"Total synthesis of cyathin A3 and cyathin B2"
(January 1, 2009).
ETD Collection for Wayne State University.
Paper AAI3337493.
http://digitalcommons.wayne.edu/dissertations/AAI3337493
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