Enantioselective Formal Total Synthesis of Roseophilin

An enantioselective formal total synthesis of roseophilin 3 is presented. The 13-membered ring of macrotricycle 1 was formed via an efficient ring-closing metathesis reaction of bicycle 4. A palladium-catalyzed methoxycarbonylation reaction of enol triflate 5 was utilized to functionalize the right-...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2000-04, Vol.2 (8), p.1157-1160
Main Authors: Bamford, Samantha J, Luker, Tim, Speckamp, W. Nico, Hiemstra, Henk
Format: Article
Language:English
Subjects:
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
Streptomyces - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An enantioselective formal total synthesis of roseophilin 3 is presented. The 13-membered ring of macrotricycle 1 was formed via an efficient ring-closing metathesis reaction of bicycle 4. A palladium-catalyzed methoxycarbonylation reaction of enol triflate 5 was utilized to functionalize the right-hand ring of bicycle 2. The allyl substituent was introduced by a radical allylation of α-bromoketone 17.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005750s