Elsevier

Tetrahedron Letters

Volume 34, Issue 36, 3 September 1993, Pages 5685-5688
Tetrahedron Letters

Indolocarbazoles. 2. Synthetic studies towards staurosporine. An unexpected 1,2 migration of indolocarbazole nitrogen results in a novel and potent Protein kinase C inhibitor.

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Abstract

Attempted transformation of the readily accessible cyclofuransylated indolocarbazole (4) to a cyclopyranosylated compound related to 1 was explored. An unexpected rearranged product (10) was obtained from (9). Compound (10) was converted to (14), a potent PKC inhibitor. The mechanism of the rearrangement was unraveled with a deuterium labeling experiment.

Attempted ring expansion (4) to a cyclopyranoslated compound, led to an unusual rearrangement [(9) to (10)]. (10) was converted to (14).

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