Total synthesis of schilancitrilactones b and C

Liang Wang; Hengtao Wang; Yihang Li; Pingping Tang

doi:10.1002/anie.201501169

Total synthesis of schilancitrilactones b and C

Angew Chem Int Ed Engl. 2015 May 4;54(19):5732-5. doi: 10.1002/anie.201501169. Epub 2015 Mar 13.

Authors

Liang Wang¹, Hengtao Wang, Yihang Li, Pingping Tang

Affiliation

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (China).

PMID: 25773236
DOI: 10.1002/anie.201501169

Abstract

The first total syntheses of schilancitrilactones B and C have been accomplished in 17 steps (longest linear sequence) from commercially available materials. Key steps include an intramolecular radical cyclization to provide the seven-membered ring, late-stage iodination, and an intermolecular radical addition reaction to complete the total synthesis.

Keywords: cyclizations; natural products; radical chemistry; terpenoids; total synthesis.

Publication types

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

MeSH terms

Molecular Conformation
Stereoisomerism
Triterpenes / chemical synthesis*
Triterpenes / chemistry

Substances

Triterpenes
schilancitrilactone B
schilancitrilactone C