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Synlett 2000; 2000(1): 53-56
DOI: 10.1055/s-2000-6455
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Stereoselective Synthesis of (-)-Swainsonine and 1,2-di-epi-Swainsonine from γ-Hydroxy-α,β-unsaturated Sulfones

Javier de Vicente* , Ramón Gómez Arrayás, Javier Cañada, Juan Carlos Carretero
  • *Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain; Fax + 34 9 13 97 39 66; E-mail: juancarlos.carretero@uam.es
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Publication Date:
31 December 2000 (online)

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Efficient and stereodivergent syntheses of (-)-swainsonine and 1,2-di-epi-swainsonine starting from the readily available enantiomerically pure γ-hydroxy-α,β-unsaturated sulfone (R)-2 are described. The stereoselectivity in the osmium-dihydroxylation step of the unsaturated indolizidines 8 was highly dependent on the substitution at C8. 1,2-di-epi-swainsonine was found to be a good inhibitor of α-d-mannosidase (jack bean).

swainsonine - sulfones - stereoselectivity - glycosidase inhibitors - lipases

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