Group 4 metals in polyketide synthesis: a convergent strategy for the synthesis of polypropionate-derived (E,E)-trisubstituted 1,3-dienes

Heidi L Shimp; Glenn C Micalizio

doi:10.1021/ol052241n

Group 4 metals in polyketide synthesis: a convergent strategy for the synthesis of polypropionate-derived (E,E)-trisubstituted 1,3-dienes

Org Lett. 2005 Oct 27;7(22):5111-4. doi: 10.1021/ol052241n.

Authors

Heidi L Shimp¹, Glenn C Micalizio

Affiliation

¹ Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.

PMID: 16235970
DOI: 10.1021/ol052241n

Abstract

[reaction: see text] A convergent Group 4 metal-mediated coupling process is described for the synthesis of polypropionate-derived (E,E)-1,3-dienes. Both the stereochemistry of the internal alkyne and the presence/absence of a tethered alkoxide on this pi-component were found to play critical roles in dictating the regiochemical course of these reactions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Propionates / chemical synthesis*
Propionates / chemistry
Stereoisomerism
Transition Elements / chemistry*

Substances

Alkenes
Macrolides
Propionates
Transition Elements