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Formal total synthesis of (±)-cortistatin A.

ABSTRACT: A second-generation synthesis of the pentacyclic core of the cortistatins, a family of rearranged steroidal alkaloids that have recently attracted much attention, is reported. The improved sequence provides access to significant quantities of this key compound, which enabled a formal total synthesis of (±)-cortistatin A by conversion to the key Nicolaou/Hirama dienone. It is anticipated that this new, robust route to the pentacyclic core will facilitate the total synthesis of a range of natural products in the cortistatin family, as well as the construction of key structural analogs to probe the promising biological activity of these important compounds.

SUBMITTER: Simmons EM 

PROVIDER: S-EPMC2909620 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Formal total synthesis of (±)-cortistatin A.

Simmons Eric M EM   Hardin-Narayan Alison R AR   Guo Xuelei X   Sarpong Richmond R  

Tetrahedron 20100601 26

A second-generation synthesis of the pentacyclic core of the cortistatins, a family of rearranged steroidal alkaloids that have recently attracted much attention, is reported. The improved sequence provides access to significant quantities of this key compound, which enabled a formal total synthesis of (±)-cortistatin A by conversion to the key Nicolaou/Hirama dienone. It is anticipated that this new, robust route to the pentacyclic core will facilitate the total synthesis of a range of natural  ...[more]

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