Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus

Dustin J Mergott; Scott A Frank; William R Roush

doi:10.1021/ol026540d

Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus

Org Lett. 2002 Sep 5;4(18):3157-60. doi: 10.1021/ol026540d.

Authors

Dustin J Mergott¹, Scott A Frank, William R Roush

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055.

PMID: 12201741
DOI: 10.1021/ol026540d

Abstract

[reaction: see text] A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels-Alder reaction and intramolecular vinylogous Morita-Baylis-Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Cyclization
Insecticides / chemical synthesis
Macrolides*
Saccharopolyspora / chemistry
Stereoisomerism
Vinyl Compounds / chemistry

Substances

Anti-Bacterial Agents
Insecticides
Macrolides
Vinyl Compounds
spinosyn A

Grants and funding

GM 26782/GM/NIGMS NIH HHS/United States