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• Vilotijevic, I
• Jamison, TF.
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• Jamison, TF.
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• Vilotijevic, I
• Jamison, TF.

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Mar. Drugs 2010, 8(3), 763-809; doi:10.3390/md8030763

Review

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

Ivan Vilotijevic and Timothy F. Jamison*

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA

* Author to whom correspondence should be addressed.

Received: 25 February 2010; in revised form: 11 March 2010 / Accepted: 18 March 2010 / Published: 19 March 2010

(This article belongs to the Special Issue Marine Dinoflagellates)

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Abstract: The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.

Keywords: marine polyethers; epoxide-opening cascades; biomimetic synthesis

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