Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives

Hussain, Mulla Althafh and Khan, Faiz Ahmed (2019) Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives. Tetrahedron Letters. p. 151040. ISSN 00404039

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Abstract

A full account of the total synthesis of aspidostomide B, C, their analogues and our synthetic efforts towards the synthesis of aspidostomide D, which led to the synthesis of regioisomeric N-methyl aspidostomide D, its analogues via epoxide opening strategy is presented. The synthesis of regioisomeric N-methyl aspidostomide D involves an efficient, five-step sequence, with 36.3% overall yield, starting from 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid. The key features of this protocol are intramolecular cyclization, dehydration, oxidation, and a Lewis acid-mediated regioselective epoxide ring opening by C-3 position of 2,5-dibromo-1H-indole to furnish the title compounds.

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