Journal
TETRAHEDRON
Volume 66, Issue 26, Pages 4696-4700Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.01.030
Keywords
Cortistatin A; Formal total synthesis; Cycloisomerization; Oxidative dearomatization; Angiogenesis
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Funding
- UC Berkeley
- Eli Lilly [2007-2008]
- GlaxoSmithKline
- AstraZeneca
- ACS Division of Medicinal Chemistry
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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