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Total Synthesis of Natural and Non-Natural Delta(5,6)Delta(12,13)-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

Schnabel, C., Sterz, K., Müller, H., Rehbein, Julia, Wiese, M. and Hiersemann, M. 2011. Total Synthesis of Natural and Non-Natural Delta(5,6)Delta(12,13)-Jatrophane Diterpenes and Their Evaluation as MDR Modulators. Journal of Organic Chemistry 76 (2) , pp. 512-522. 10.1021/jo1019738

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Abstract

We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki−Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl−ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 0022-3263
Last Modified: 19 Mar 2016 22:21
URI: http://orca-mwe.cf.ac.uk/id/eprint/13006

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