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Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

2006; Elsevier BV; Volume: 62; Issue: 13 Linguagem: Inglês

10.1016/j.tet.2006.01.036

1464-5416

Oscar R. Suárez‐Castillo, M. Sanchez-Zavala, M. Melendez‐Rodriguez, L.E. Castelan-Duarte, Martha S. Morales‐Ríos, Pedro Joseph‐Nathan,

Bioactive Compounds and Antitumor Agents

This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7).