Issue 3, 1998

Convenient methods for regio- and/or chemo-selective O-deacylation of taxinine, a naturally occurring taxane diterpenoid

Abstract

Selective O-deacylations of taxinine 1a, readily available from needles of Taxus cuspidata, at C-2, C-5 and C-9,10 have been accomplished by treatment with barium hydroxide octahydrate, sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al® ) or diisobutylaluminium hydride (DIBAL-H) under mild conditions to give 2,9,10-tri-O-deacetyltaxinine 4b, 2-O-deacetyltaxinine 4c, 5-O-decinnamoyltaxinine (taxinine A, 5a) and 2,5-di-O-deacyltaxinine (taxuspine G, 5b), respectively, which are expected to be useful synthetic intermediates for biologically active taxinine derivatives.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 417-422

Convenient methods for regio- and/or chemo-selective O-deacylation of taxinine, a naturally occurring taxane diterpenoid

M. Sako, H. Suzuki, N. Yamamoto, K. Hirota and Y. Maki, J. Chem. Soc., Perkin Trans. 1, 1998, 417 DOI: 10.1039/A707146I

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