TOTAL SYNTHESIS OF UPIAL, A MARINE SESQUITERPENE POSSESSING BICYCLO[3.3.1]NONANE RING-SYSTEM

Authors
NAGAOKA H SHIBUYA K YAMADA Y
Citation
H. Nagaoka et al., TOTAL SYNTHESIS OF UPIAL, A MARINE SESQUITERPENE POSSESSING BICYCLO[3.3.1]NONANE RING-SYSTEM, Tetrahedron, 50(3), 1994, pp. 661-688
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
3
Year of publication
1994
Pages
661 - 688
Database
ISI
SICI code
0040-4020(1994)50:3<661:TSOUAM>2.0.ZU;2-I
Abstract
The total synthesis of marine sesquiterpene upial wets achieved starti ng from D-mannitol via sequential Michael reaction of the lithium enol ate of 5 with methyl 2-dimethyl-1,3-dioxolan-4-yl)-2-pentenoate((E)-6) , fragmentation reaction of tricyclic compound 22 and samarium((li iod ide-induced cyclization of diformate 3.