Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure

Kwangho Kim; Umar S M Maharoof; Jessica Raushel; Gary A Sulikowski

doi:10.1021/ol034823f

Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure

Org Lett. 2003 Aug 7;5(16):2777-80. doi: 10.1021/ol034823f.

Authors

Kwangho Kim¹, Umar S M Maharoof, Jessica Raushel, Gary A Sulikowski

Affiliation

¹ Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.

PMID: 12889872
DOI: 10.1021/ol034823f

Abstract

[reaction: see text] Intramolecular Diels-Alder cycloaddition of tolylsulfonyl alkynone 5a and vinyl ketone 19 led to single isomers with opposite diastereoselectivity. Decalin 20 incorporates the correct C(9)-C(11) stereochemical array for a projected synthesis of HMP-Y1 (1).

Publication types

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

MeSH terms

Molecular Structure*
Stereoisomerism

Grants and funding

CA59515-06/CA/NCI NIH HHS/United States