Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge

Concise synthesis of BC-ring model compounds of 13E, 17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity. (C) 2008 Elsevier Ltd. All rights reserved.