Convenient methods for regio- and/or chemo-selective O-deacylation of taxinine, a naturally occurring taxane diterpenoid
作者： Magoichi Sako , Hikokazu Suzuki , Noriyuki Yamamoto , Kosaku Hirota , Yoshifumi Maki
DOI: 10.1039/A707146I
关键词: Chemistry 、 Aluminium hydride 、 Barium hydroxide octahydrate 、 Taxus cuspidata 、 Sodium 、 Terpenoid 、 Taxane 、 Diisobutylaluminium hydride 、 Taxuspine 、 Organic chemistry
摘要: Selective O-deacylations of taxinine 1a, readily available from needles 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 (DIBAL-H) under mild conditions to give 2,9,10-tri-O-deacetyltaxinine 4b, 2-O-deacetyltaxinine 4c, 5-O-decinnamoyltaxinine (taxinine A, 5a) 2,5-di-O-deacyltaxinine (taxuspine G, 5b), respectively, which are expected be useful synthetic intermediates for biologically active derivatives.
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