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A new efficient synthesis of taxol A-ring synthon via two aldol condensations

✍ Scribed by Chang-Qing Wei; Xiang-Rong Jiang; Yu Ding

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
374 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

An efficient stereocontrolled synthesis of a taxol A-ring synthon using two aldol reactions as key steps is presented.

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New synthesis of a taxol A-ring system.
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3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-a-D-xylo-hexadialdo-1,4-furanose (2) upon treatment with Lirv(TMS)2 at -500 furnished the e&ate which reacted with methyl 2,3,4-tri-Obenzyl-a-D-glucopyranoside-6-ulose (5) to afford two eythro aldols 3 and 4 in 6:l ratio and 43% yield. 5R;6R Confguration was a