An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one: a formal synthesis of (+/-)-mesembranol

Authors
Evarts, JB Fuchs, PL
Citation
Jb. Evarts et Pl. Fuchs, An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one: a formal synthesis of (+/-)-mesembranol, TETRAHEDR L, 42(22), 2001, pp. 3673-3675
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
22
Year of publication
2001
Pages
3673 - 3675
Database
ISI
SICI code
0040-4039(20010528)42:22<3673:AEACSO>2.0.ZU;2-K
Abstract
Inexpensive enantiopure (+)-limonene oxide 1 is converted to 4-(R)-(t-butyl dimethylsilyloxy)-cyclohex-2-en-1-one 2a. All isolated intermediates can be distilled obviating the need for chromatography. With 2a,b in hand, a form al synthesis of (+/-)-mesembranol 17 using vinyl triflate methodology is hi gh) yielding. (C) 2001 Elsevier Science Ltd. All rights reserved.