Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement

Authors
Smith, AB Verhoest, PR Minbiole, KP Lim, JJ
Citation
Ab. Smith et al., Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement, ORG LETT, 1(6), 1999, pp. 909-912
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
6
Year of publication
1999
Pages
909 - 912
Database
ISI
SICI code
1523-7060(19990923)1:6<909:PSS1CO>2.0.ZU;2-I
Abstract
[GRAPHICS] In this, the first of two Letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and a (2), rare oxazole containing m acrolides possessing extraordinary antimitotic activity, and describe the a ssembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazol e A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yi eld), exploiting a modification of the Petasis-Ferrier rearrangement to con struct the C(11-15) cis-tetrahydropyran, Dimethylaluminum chloride (Me2AlCl ) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangeme nt.