Stereoselective synthesis of oxa- and aza-angular triquinanes using tandem radical cyclization to vinylogous carbonates and carbamates

Santosh J Gharpure; P Niranjana; Suheel K Porwal

doi:10.1021/ol302557a

Stereoselective synthesis of oxa- and aza-angular triquinanes using tandem radical cyclization to vinylogous carbonates and carbamates

Org Lett. 2012 Nov 2;14(21):5476-9. doi: 10.1021/ol302557a. Epub 2012 Oct 25.

Authors

Santosh J Gharpure¹, P Niranjana, Suheel K Porwal

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India. sjgharpure@iitb.ac.in

PMID: 23098225
DOI: 10.1021/ol302557a

Abstract

Tandem radical cyclization to vinylogous carbonates and carbamates is developed for a new, highly stereoselective synthesis of heterocyclic angular triquinanes. The strategy is also useful to gain access to oxa- and azatriquinanes, which incorporate the spiroindoline moiety. The method is further extended to the synthesis of lactone-bearing as well as uracil-fused angular triquinanes.

Publication types

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

MeSH terms

Aza Compounds / chemical synthesis*
Aza Compounds / chemistry
Carbamates / chemistry*
Carbonates / chemistry*
Combinatorial Chemistry Techniques
Cyclization
Molecular Structure
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry

Substances

Aza Compounds
Carbamates
Carbonates
Sesquiterpenes