TOTAL SYNTHESIS OF TAXOL .4. THE FINAL STAGES AND COMPLETION OF THE SYNTHESIS

Authors
NICOLAOU KC UENO H LIU JJ NANTERMET PG YANG Z RENAUD J PAULVANNAN K CHADHA R
Citation
Kc. Nicolaou et al., TOTAL SYNTHESIS OF TAXOL .4. THE FINAL STAGES AND COMPLETION OF THE SYNTHESIS, Journal of the American Chemical Society, 117(2), 1995, pp. 653-659
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
117
Issue
2
Year of publication
1995
Pages
653 - 659
Database
ISI
SICI code
0002-7863(1995)117:2<653:TSOT.T>2.0.ZU;2-Z
Abstract
The total synthesis of (-)-Taxol has been achieved. Functional group m anipulation of diol 2 provided the ABC ring system with the correct C9 -keto, C10-acetyloxy functionality. Careful optimization allowed the o xidation of the C5-C6 alkene in 4 at C5 via a hydroboration reaction. Functional group manipulation of this product, 29, provided, through t wo routes, the oxetane D ring as 36. Following the method developed by degradative studies provided the natural enantiomer of Taxol (1).