An efficient synthesis of highly functionalized [5,6] aromatic spiroketals by hetero-Diels-Alder reaction

Guanglian Zhou; Jianrong Zhu; Zhixiang Xie; Ying Li

doi:10.1021/ol7029068

An efficient synthesis of highly functionalized [5,6] aromatic spiroketals by hetero-Diels-Alder reaction

Org Lett. 2008 Mar 6;10(5):721-4. doi: 10.1021/ol7029068. Epub 2008 Feb 12.

Authors

Guanglian Zhou¹, Jianrong Zhu, Zhixiang Xie, Ying Li

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.

PMID: 18266379
DOI: 10.1021/ol7029068

Abstract

A hetero-Diels-Alder reaction of vinyl sulfoxides with o-quinone methides precursor constructs highly functionalized [5,6] aromatic spiroketal skeletons in moderate to good yields with high regioselectivity. The two functional groups (ketone and olefin) can be further subjected to many synthetic transformations.

Publication types

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

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Cyclization
Furans / chemical synthesis*
Furans / chemistry
Models, Molecular
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Styrenes / chemistry

Substances

Furans
Spiro Compounds
Styrenes
spiroketal