- Asymmetric total synthesis of (-)-lupinine and (+)-epilupinine via α-sulfinyl ketimine. Stereocontrolled reduction of β-sulfinyl enamines
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(-)-Lupinine and (+)-epilupinine [(1R,9aR)- and (1S,9aR)-octahydro-1-hydroxymethyl-2H-quinolizine] were synthesized from (+)-2,3,4,5-tetrahydro-6-[(R)-(4-methylphenyl)sulfinylmethyl]pyridine (4) in five steps. The intermediate, 3,4,6,7,8,9-hexahydro-1-[(R)-(4-methylphenyl)sulfinyl]-2H-quinolizine (7), was stereoselectively reduced with cerium(III) chloride heptahydrate and sodium borohydride to give predominantly C-9a-R isomers, (9aR)-octahydro-1-[(R)-(4-methylphenyl)sulfinyl]-2H-quinolizines.
- Hua,Miao,Bravo,Takemoto
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p. 970 - 974
(2007/10/02)
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