Stereoselective total syntheses of alpha,beta-unsaturated delta-lactones having a 1,3-syn-polyol moiety, isolated from Cryptocarya latifolia

Authors
Jorgensen, KB Suenaga, T Nakata, T
Citation
Kb. Jorgensen et al., Stereoselective total syntheses of alpha,beta-unsaturated delta-lactones having a 1,3-syn-polyol moiety, isolated from Cryptocarya latifolia, TETRAHEDR L, 40(50), 1999, pp. 8855-8858
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
50
Year of publication
1999
Pages
8855 - 8858
Database
ISI
SICI code
0040-4039(199912)40:50<8855:STSOAD>2.0.ZU;2-W
Abstract
The first total syntheses of two alpha,beta-unsaturated glactones having a 1,3-syn-polyol moiety, isolated from Cryptocarya latifolia, were achieved. The key reactions include the Sharpless asymmetric epoxidation of the allyl alcohol, stereoselective addition of an allyl group to the epoxy aldehyde, regioselective reduction of the epoxy ring, and formation of the alpha,bet a-unsaturated delta-lactone. (C) 1999 Elsevier Science Ltd. All rights rese rved.