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Synthesis 1991; 1991(11): 970-974
DOI: 10.1055/s-1991-26620
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Asymmetric Total Synthesis of (-)-Lupinine and (+)-Epilupinine via α-Sulfinyl Ketimine. Stereocontrolled Reduction of β-Sulfinyl Enamines

Duy H. Hua* , Shou Wu Miao, Ana A. Bravo, Dolores J. Takemoto
  • *Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA
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Publication Date:
29 April 2002 (online)

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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.

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