Exploiting the reversibility of olefin metathesis. Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin

Authors
Furstner, A Thiel, OR Ackermann, L
Citation
A. Furstner et al., Exploiting the reversibility of olefin metathesis. Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin, ORG LETT, 3(3), 2001, pp. 449-451
Citations number
44
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
449 - 451
Database
ISI
SICI code
1523-7060(20010208)3:3<449:ETROOM>2.0.ZU;2-W
Abstract
[GRAPHICS] The formation of the trisubstituted cycloalkene 7 by RCM of diene 5 proceed s via the acyclic dimer 6, thus demonstrating the ready reversibility of ol efin metathesis if catalyzed by "second generation" ruthenium carbene compl exes such as 2-4. When applied to acrylate 11, these catalysts trigger a cy clooligomerization process that evolves with time and serves as key step en route to the lactide antibiotic (-)-pyrenophorin 8.