Synthesis of the C20-C26 building block of halichondrins via a regiospecific and stereoselective S(N)2' reaction

Chaoyu Xie; Pawel Nowak; Yoshito Kishi

doi:10.1021/ol026982p

Synthesis of the C20-C26 building block of halichondrins via a regiospecific and stereoselective S(N)2' reaction

Org Lett. 2002 Dec 12;4(25):4427-9. doi: 10.1021/ol026982p.

Authors

Chaoyu Xie¹, Pawel Nowak, Yoshito Kishi

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

PMID: 12465904
DOI: 10.1021/ol026982p

Abstract

[reaction: see text] A regiospecific and stereoselective S(N)2' reaction to convert the trisylate into the vinyl iodide is presented. The homoallylic alcohol is used to direct the delivery of LiCu(Me)(2).

Publication types

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

MeSH terms

Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry*
Stereoisomerism

Substances

Ethers, Cyclic

Grants and funding

CA 22215/CA/NCI NIH HHS/United States