A Multiply Convergent Platform for the Synthesis of Trioxacarcins

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A Multiply Convergent Platform for the Synthesis of Trioxacarcins

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Title: A Multiply Convergent Platform for the Synthesis of Trioxacarcins
Author: Myers, Andrew G.; Švenda, Jakub; Hill, Nicholas

Note: Order does not necessarily reflect citation order of authors.

Citation: Švenda, Jakub, Nicholas Hill, and Andrew G. Myers. 2011. A multiply convergent platform for the synthesis of trioxacarcins. Proceedings of the National Academy of Sciences of the United States of America 108(17): 6709–6714.
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Abstract: Many first-line cancer drugs are natural products or are derived from them by chemical modification. The trioxacarcins are an emerging class of molecules of microbial origin with potent antiproliferative effects, which may derive from their ability to covalently modify duplex DNA. All trioxacarcins appear to be derivatives of a non-glycosylated natural product known as DC-45-A2. To explore the potential of the trioxacarcins for the development of small-molecule drugs and probes, we have designed a synthetic strategy towards the trioxacarcin scaffold that enables access to both the natural trioxacarcins and non-natural structural variants. Here we report a synthetic route to DC-45-A2 from a differentially protected precursor, which in turn is assembled in just six steps from three components of similar structural complexity. The brevity of the sequence arises from strict adherence to a plan in which strategic bond-pair constructions are staged at or near the end of the synthetic route.
Published Version: doi:10.1073/pnas.1015257108
Terms of Use: This article is made available under the terms and conditions applicable to Other Posted Material, as set forth at http://nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of-use#LAA
Citable link to this page: http://nrs.harvard.edu/urn-3:HUL.InstRepos:5125260
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