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Transformation of D : A-Friedo-18β-lup-19-en-3-one into D : B-Friedo-18β,19αH-lup-5-en-3β-ol and a Comment on the Structure of Guimarenol

Abstract D:A-friedo-18β-lup-19-en-3-one was transformed into D:B-Friedo-18β,19αH-lup-5-en-3β-ol by two routes, 1) bromination-dehydrobromination of an enol benzoate of D:A-friedo-18β,19αH-lupan-3-one and 2) BF3·Et2O-catalyzed backbone rearrangement of 3β,4β-epoxy-D:A-friedo-18β, 19αH-lupane. The 18βH,19αH-configuration in these D:A- and D:B-friedo-type lupane derivatives was determined by means of X-ray diffraction for a 3α,4α-epoxide derived from D:A-friedo-18β,19αH-lupan-3β-ol. The synthetic D:B-friedo-18β,19βH-lup-5-en-3β-ol was found to be not identical with guimarenol isolated from Ceropegia dichotoma.

Oxford University Press (OUP)

Yasushi Yokoyama Yoshihiko Moriyama Takahiko Tsuyuki Takeyoshi Takahashi Akiko Itai Yoichi Iitaka

Bulletin of the Chemical Society of Japan

2006

Title: Transformation of D : A-Friedo-18β-lup-19-en-3-one into D : B-Friedo-18β,19αH-lup-5-en-3β-ol and a Comment on the Structure of Guimarenol

Description:

The 18βH,19αH-configuration in these D:A- and D:B-friedo-type lupane derivatives was determined by means of X-ray diffraction for a 3α,4α-epoxide derived from D:A-friedo-18β,19αH-lupan-3β-ol.

The synthetic D:B-friedo-18β,19βH-lup-5-en-3β-ol was found to be not identical with guimarenol isolated from Ceropegia dichotoma.

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Transformation of D : A-Friedo-18β-lup-19-en-3-one into D : B-Friedo-18β,19αH-lup-5-en-3β-ol and a Comment on the Structure of Guimarenol

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