Migrated Lupane Derivatives. Boron Trifluoride Etherate-catalyzed Backbone Rearrangement of 3α,4α- and 3β,4β-Epoxy-D:A-friedo-18β,19αH-lupanes and Solvent Effects

DOI: 10.1246/bcsj.54.234

Source and publish data:

Bulletin of the Chemical Society of Japan p. 234 - 239 (1981)

Update date:2022-08-04

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Authors:

Yokoyama, Yasushi

Moriyama, Yoshihiko

Tsuyuki, Takahiko

Takahashi, Takeyoshi

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Article abstract of DOI:10.1246/bcsj.54.234

Backbone rearrangements of 3α,4α- and 3β,4β-epoxy-D:A-friedo-18β,19αH-lupanes catalyzed by boron trifluoride etherate gave 18β,19αH-lup-12-en-3-ols, lup-18-en-3-ols, and lup-19-en-3-ols besides known D:B-friedo-18β,19αH-lup-5-en-3-ols and -5(10)-en-3-ols.D:B-Friedo-18β,19αH-lup-1(10)-en-3α-ol and 3β,10β-epoxy-D:B-friedo-18β,19αH-lupane were also obtained from α- and β-epoxides, respectively.Solvent effects on these reactions were examined.

Full text of DOI:10.1246/bcsj.54.234

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