Formal [4+2]-annulation of chiral crotylsilanes: Synthesis of the C19-C28 fragment of phorboxazoles

Authors
Huang, HB Panek, JS
Citation
Hb. Huang et Js. Panek, Formal [4+2]-annulation of chiral crotylsilanes: Synthesis of the C19-C28 fragment of phorboxazoles, ORG LETT, 3(11), 2001, pp. 1693-1696
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
11
Year of publication
2001
Pages
1693 - 1696
Database
ISI
SICI code
1523-7060(20010531)3:11<1693:F[OCCS>2.0.ZU;2-I
Abstract
A stereoselective synthesis of the C19-C28 fragment of phoborxazole A and a is described. The key step is an enantioselective [4 + 2]-annulation of a crotylsilane 10 with a propargylic aldehyde 11 affording a functionalized d ihydropyran 12. A solvent dependent stereoselective epoxidation of dihydrop yrans is also documented.