Tandem alkylation-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans

Santosh J Gharpure; S Raja Bhushan Reddy

doi:10.1021/ol900721q

Tandem alkylation-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans

Org Lett. 2009 Jun 18;11(12):2519-22. doi: 10.1021/ol900721q.

Authors

Santosh J Gharpure¹, S Raja Bhushan Reddy

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Madras, Chennai - 600036, India. sjgharpure@iitm.ac.in

PMID: 19445488
DOI: 10.1021/ol900721q

Abstract

A stereoselective method for the synthesis of substituted tetrahydropyran derivatives employing a tandem S(N)2-Michael addition sequence to vinylogous carbonates is developed. The method is extended to the synthesis of bicyclic ether motifs present in polyether ladder toxins.

Publication types

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

MeSH terms

Alkylation
Crystallography, X-Ray
Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry
Models, Molecular
Pyrans / chemical synthesis*
Pyrans / chemistry
Stereoisomerism
Vinyl Compounds / chemistry*

Substances

Ethers, Cyclic
Pyrans
Vinyl Compounds