Palladium-induced cyclizations for the synthesis of cis-2,5-disubstituted-3-methylenetetrahydrofurans: studies of the C7-C22 core of amphidinolide K

D R Williams; K G Meyer

doi:10.1021/ol990255l

Palladium-induced cyclizations for the synthesis of cis-2,5-disubstituted-3-methylenetetrahydrofurans: studies of the C7-C22 core of amphidinolide K

Org Lett. 1999 Oct 21;1(8):1303-5. doi: 10.1021/ol990255l.

Authors

D R Williams¹, K G Meyer

Affiliation

¹ Department of Chemistry, Indiana University, Bloomington 47405-7102, USA. williamd@indiana.edu

PMID: 10825979
DOI: 10.1021/ol990255l

Abstract

[formula: see text] The diastereoselective synthesis of cis-2,5-disubstituted-3-methylenetetrahydrofurans via Pd(0)-catalyzed cyclization of 2-methylene-1,4-diols is described. Investigations into the scope of the reaction and its application toward the synthesis of amphidinolide K is reported.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Catalysis
Furans / chemical synthesis*
Furans / chemistry
Macrolides
Magnetic Resonance Spectroscopy
Molecular Structure
Palladium / chemistry*

Substances

Bridged Bicyclo Compounds, Heterocyclic
Furans
Macrolides
amphidinolide K
tetrahydrofuran
Palladium

Grants and funding

GM-42897/GM/NIGMS NIH HHS/United States