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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Construction the A-B Bicyclic Ring Structure of Stemocurtisine

Author(s): Duc Dau Xuan*

Volume 18, Issue 1, 2021

Published on: 07 February, 2020

Page: [58 - 65] Pages: 8

DOI: 10.2174/1570178617666200207105649

Price: $65

Abstract

In this paper, the synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearrangement under different basic conditions were unsuccessful. The only unreactive starting material was recovered.

Keywords: Stemoma alkaloid, Semocurtisine, Glutamic acid, borono-Mannich reaction, 6-membered ring lactone, epoxide.

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