Elsevier

Tetrahedron Letters

Volume 35, Issue 19, 9 May 1994, Pages 3005-3008
Tetrahedron Letters

Indolocarbazoles. 4. Synthetic studies towards staurosporine and tjipanazoles: Reactions of indolocarbazole with glycals

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Abstract

In an attempt to construct the unique N,N′-bidentate glycosyl linkage found in the Staurosporine 1 class of natural products, the first example of an acid catalyzed 2,6-condensation of an activated pyran with indolocarbazole 4 is reported. In pursuit of the real system, a variety of glycals were reacted with indolocarbazole 4. Formation of novel unexpected products (B/C) with 1,3-connections along with the expected product (A) and its' synthetic transformation to a potentially useful intermediate 24 are detailed.

Our efforts to synthesize Staurosporine analogs by reacting indolocarbazole 4 with a variety of glycals leading to B/C and/or A type products, along with the synthesis of the parent system 9 are described. One of the A type products was transformed to 24, a potentially useful intermediate.

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