Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of gamma-chiral (Z)-enals

Authors
Paterson, I Florence, GJ
Citation
I. Paterson et Gj. Florence, Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of gamma-chiral (Z)-enals, TETRAHEDR L, 41(35), 2000, pp. 6935-6939
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
35
Year of publication
2000
Pages
6935 - 6939
Database
ISI
SICI code
0040-4039(20000826)41:35<6935:SO(AAB>2.0.ZU;2-Z
Abstract
The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with hi gh levels of 1,4-stereo-induction arising from the gamma-substituent. Reage nt control from (+)-Ipc(2)BCl can be used effectively to overturn this subs trate bias, thus enabling the stereocontrolled formation of (+)-discodermol ide (1) and related analogues 15-18. (C) 2000 Elsevier Science Ltd. All rig hts reserved.