Enantioselective formal total synthesis of roseophilin

Authors
Bamford, SJ Luker, T Speckamp, WN Hiemstra, H
Citation
Sj. Bamford et al., Enantioselective formal total synthesis of roseophilin, ORG LETT, 2(8), 2000, pp. 1157-1160
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
8
Year of publication
2000
Pages
1157 - 1160
Database
ISI
SICI code
1523-7060(20000420)2:8<1157:EFTSOR>2.0.ZU;2-G
Abstract
An enantioselective formal total synthesis of roseophilin 3 is presented. T he 13-membered ring of macrotricycle 1 was formed via an efficient ring-clo sing metathesis reaction of bicycle 4. A palladium-catalyzed methoxycarbony lation reaction of enol triflate 5 was utilized to functionalize the right- hand ring of bicycle 2. The allyl substituent was introduced by a radical a llylation of alpha-bromoketone 17.