Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration.
The first stereoselective total synthesis of the bibenzyl tetrahydrocannabinol, (-)-perrottetinene, has been achieved from readily available starting materials. The absolute stereochemistry is derived from a chiral gamma-hydroxy vinylstannane. The key reaction is the synthesis of the cis-disubstituted cyclohexene ring of perrottetinene by diastereoselective Ireland-Claisen rearrangement and a ring-closing metathesis reaction. The absolute configuration of (-)-perrottetinene is proposed.
Song
Yanling
Y
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Hwang
Soonho
S
Gong
Ping
P
Kim
Deukjoon
D
Kim
Sanghee
S
D002188:Cannabis / Q000737:chemistry; D003500:Cyclization; D053138:Cyclohexenes / Q000737:chemistry*; D013759:Dronabinol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D053138:Cyclohexenes; C526635:perrottetinene; D013759:Dronabinol