A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol.
In one step, the skeleton of cis-spirovetivanes was constructed with high stereoselectivity by the phosphine-catalyzed [3+2] cycloaddition reaction of tert-butyl 2,3-butadienoate or 2-butynoate with 3-methyl-2-methylenecyclohexanone (5). This method was exemplified by the first highly efficient total synthesis of natural product (-)-hinesol, which is an active ingredient of cerebral circulation and metabolism improvers.
Du
Yishu
Y
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Lu
Xiyan
X
D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D010720:Phosphines / Q000737:chemistry*; D012717:Sesquiterpenes; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010720:Phosphines; D012717:Sesquiterpenes; D013141:Spiro Compounds; C065858:hinesol