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ACS Cent Sci. 2017 Jan 25;3(1):47-51. doi: 10.1021/acscentsci.6b00313. Epub 2016 Dec 19.

Scalable Synthesis of (-)-Thapsigargin.

Author information

1
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
2
Front End Innovation, LEO Pharma , A/S Industriparken 55, 2750 Ballerup, Denmark.

Abstract

Total syntheses of the complex, highly oxygenated sesquiterpenes thapsigargin (1) and nortrilobolide (2) are presented. Access to analogues of these promising bioactive natural products has been limited to tedious isolation and semisynthetic efforts. Elegant prior total syntheses demonstrated the feasibility of creating these entitites in 36-42 step processes. The currently reported route proceeds in a scalable and more concise fashion by utilizing two-phase terpene synthesis logic. Salient features of the work include application of the classic photosantonin rearrangement and precisely choreographed installation of the multiple oxygenations present on the guaianolide skeleton.

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