The Synthesis of Lupin Alkaloids. II. A Formal Synthesis of (±) -Sparteine

NORIYUKI TAKATSU; MASAYO NOGUCHI; SHIGERU OHMIYA; HIROTAKA OTOMASU

doi:10.1248/cpb.35.4990

NORIYUKI TAKATSU, MASAYO NOGUCHI, SHIGERU OHMIYA, HIROTAKA OTOMASU

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Keywords: lupin alkaloid, leontiformidine, sparteine, 8-oxosparteine, 2-hydroxyleontiformidine, 2-oxoleontiformidine, 3- (2'-piperidyl) quinolizidine, stereo-structure, Jones-oxidation

JOURNAL FREE ACCESS

1987 Volume 35 Issue 12 Pages 4990-4992

DOI https://doi.org/10.1248/cpb.35.4990

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Abstract

2-Hydroxy-3- (2'-piperidyl) quinolizidine (5), an intermediate for the synthesis of (±) -leontiformidine (1a), was converted into (±) -sparteine (7) by a three-step procedure of oxidation, Mannich reaction and deoxygenation.

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