VITAMIN-D-3 SYNTHETIC STUDIES - INTRAMOLECULAR DIELS-ALDER APPROACHESTO THE CD-RING FRAGMENT

Authors
CLASBY MC CRAIG D JAXACHAMIEC AA LAI JYQ MARSH A SLAWIN AMZ WHITE AJP WILLIAMS DJ
Citation
Mc. Clasby et al., VITAMIN-D-3 SYNTHETIC STUDIES - INTRAMOLECULAR DIELS-ALDER APPROACHESTO THE CD-RING FRAGMENT, Tetrahedron, 52(13), 1996, pp. 4769-4802
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
13
Year of publication
1996
Pages
4769 - 4802
Database
ISI
SICI code
0040-4020(1996)52:13<4769:VSS-ID>2.0.ZU;2-C
Abstract
The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a noreph edrine/dihydrocitronellic acid-derived oxazolidinone, and the intramol ecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The ana logous cycloaddition reaction of a trienylsulfone substrate is shown t o give products having the incorrect stereochemistry for vitamin D-3 s ynthesis.