1,8-stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (+/-)-epipatulolide C

Authors
Dorling, EK Thomas, AP Thomas, EJ
Citation
Ek. Dorling et al., 1,8-stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (+/-)-epipatulolide C, TETRAHEDR L, 40(3), 1999, pp. 475-476
Citations number
7
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
475 - 476
Database
ISI
SICI code
0040-4039(19990115)40:3<475:1B1UAA>2.0.ZU;2-Y
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 a 2 ,3-Wittig rearrangement: this approach has been used to complete a diastere oselective synthesis of (+/-)-epipatulolide C 16. (C) 1998 Elsevier Science Ltd. All rights reserved.