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Paper | Regular issue | Vol 83, No. 7, 2011, pp.1535-1552
Published online, 14th April, 2011
DOI: 10.3987/COM-11-12195
Synthetic Study of Carbocyclic Core of Cortistatin A, an Anti-Angiogenic Steroidal Alkaloid from Marine Sponge

Naoyuki Kotoku,* Yuji Sumii, Takeshi Hayashi, and Motomasa Kobayashi*

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan


Synthesis of carbocyclic core of cortistatin A (1), a novel anti-angiogenic steroidal alkaloid from Indonesian marine sponge, was investigated. Intramolecular Heck cyclization using substrate 18 achieved construction of 7-membered B-ring structure. The presence of steric hindrance around the reaction center was found to favor endo cyclization pathway in this substrate.