Staurosporine has interesting biological properties including antifungal and hypotensive activities. Its cytotoxic activity was based on the inhibition of protein kinase C. Herein, a new concise synthetic method towards 7-oxostaurosporine will be presented. Key features of this reaction include i) Palladium-catalyzed asymmetric addition of bis-indole to alkoxyallenes1, ii) Ruthenium-catalyzed ring closing metathesis(RCM) and iii) Ruthenium-catalyzed olefin migration of cyclic allylic acetal2. By using these reactions, Key intermediate of 7-oxostaurosporine could be obtained with high synthetic efficiency.
1) Jang, S.H. ; Kim, H.W. ; Jeong, W. ; Moon, D. ; Rhee, Y.H., Org. Lett., 2018, 4, 1248.
2) Seo, K. ; Kim, Y.J. ; Rhee, Y.H., Org. Lett., 2018, 4, 979.