1,8-stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement: Diastereoselective total synthesis of (+/-)-patulolide C

Authors
Dorling, EK Thomas, EJ
Citation
Ek. Dorling et Ej. Thomas, 1,8-stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement: Diastereoselective total synthesis of (+/-)-patulolide C, TETRAHEDR L, 40(3), 1999, pp. 471-474
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
3
Year of publication
1999
Pages
471 - 474
Database
ISI
SICI code
0040-4039(19990115)40:3<471:1B1UAA>2.0.ZU;2-1
Abstract
The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkox ypent-2-enylstannanes, which proceed with excellent 1,5-induction, with an Ireland-Claisen rearrangement: this approach has been used to complete a di astereoselective synthesis of (+/-)-patulolide C 29. (C) 1998 Elsevier Scie nce Ltd. All rights reserved.