Synthesis of the tricyclic core of aldingenin B by oxidative cyclo-ketalization of an alkyne-diol

Jingyue Yang; Jumreang Tummatorn; Rimantas Slegeris; Sami F Tlais; Gregory B Dudley

doi:10.1021/ol200421s

Synthesis of the tricyclic core of aldingenin B by oxidative cyclo-ketalization of an alkyne-diol

Org Lett. 2011 Apr 15;13(8):2065-7. doi: 10.1021/ol200421s. Epub 2011 Mar 10.

Authors

Jingyue Yang¹, Jumreang Tummatorn, Rimantas Slegeris, Sami F Tlais, Gregory B Dudley

Affiliation

¹ Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.

PMID: 21391664
DOI: 10.1021/ol200421s

Abstract

The preparation and selenium-mediated cyclo-ketalization of an alkyne-diol is described as a model study for the synthesis of aldingenin B. The oxidative cyclization is a simplifying transformation for aldingenin B, as it provides a convenient method for generating the tricylic core of the natural product from a functionalized cyclohexane.

Publication types

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

MeSH terms

Alkynes / chemistry*
Cyclization
Heterocyclic Compounds, 3-Ring / chemical synthesis*
Ketones / chemistry*
Molecular Structure
Oxidation-Reduction
Sesquiterpenes / chemical synthesis*

Substances

Alkynes
Heterocyclic Compounds, 3-Ring
Ketones
Sesquiterpenes
aldingenin B