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DOI: 10.1055/a-1768-2082
Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative
We thank Fundação para a Ciência e a Tecnologia (FCT) for project funding (PTDC/QEQ-MED/1671/2012 and SFRH/BD/87292/2012) and Fundação para a Ciência e a Tecnologia and European Fund for Regional Development FEDER-COMPETE-QREN-EU for financial support to C.Q./U.M.
Abstract
A five-step synthesis of (S)-7-hydroxy-5-aza-8a-epi-d-swainsonine [(3S,4S,4aS,5S,6R)-octahydropyrrolo[1,2-b]pyridazine-3,4,5,6-tetraol] was accessed in good overall yield from readily available d-erythrosyl benzylidene acetal buta-1,3-diene. The key step of the reaction sequence is a full stereoselective Diels–Alder cycloaddition between the diene and dienophile: diethyl azodicarboxylate (DEAD) or di-tert-butyl azodicarboxylate (DBAD). The cycloadducts were further transformed into the title 5-aza-indolizidine. Optimized procedures were obtained for the synthesis of intermediates and products.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1768-2082.
- Supporting Information
Publication History
Received: 30 November 2021
Accepted after revision: 10 February 2022
Accepted Manuscript online:
10 February 2022
Article published online:
16 March 2022
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