A formal total synthesis of roseophilin: Cyclopentannelation approach to the macrocyclic core

Authors
Harrington, PE Tius, MA
Citation
Pe. Harrington et Ma. Tius, A formal total synthesis of roseophilin: Cyclopentannelation approach to the macrocyclic core, ORG LETT, 1(4), 1999, pp. 649-651
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
4
Year of publication
1999
Pages
649 - 651
Database
ISI
SICI code
1523-7060(19990826)1:4<649:AFTSOR>2.0.ZU;2-Y
Abstract
The formal total synthesis of the macrocyclic core of roseophilin 4 has bee n accomplished in 12 steps from 5-hexenal 8, The cyclopentannelation reacti on was used to form the aliphatic five-membered ring of 3. Diene 2 was asse mbled by means of a Stetter reaction. Ring closing metathesis of 2, reducti on, and Knorr reaction of the 1,4-diketone 5 gave the ketopyrrole 3.