Synthesis of stereodefined Z-vinyl iodides from carbohydrates as a preludeto C/D ring assembly in taxanes

Authors
Paquette, LA Shih, TL Zeng, QB Hofferberth, JE
Citation
La. Paquette et al., Synthesis of stereodefined Z-vinyl iodides from carbohydrates as a preludeto C/D ring assembly in taxanes, TETRAHEDR L, 40(18), 1999, pp. 3519-3522
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
18
Year of publication
1999
Pages
3519 - 3522
Database
ISI
SICI code
0040-4039(19990430)40:18<3519:SOSZIF>2.0.ZU;2-Z
Abstract
D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontroll ed vinylation, oxidative fragmentation of the tetrahydrofuran-2,3-diol, oxe tane ring closure, and highly stereoselective iodoolefination. (C) 1999 Els evier Science Ltd. All rights reserved.