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Stereoselective syntheses of the octahydropyrano[2,3-b]pyridine DE core of 'Upenamide via a stannous chloride-induced deacetalisation-cyclisation procedure

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JournalEuropean Journal of Organic Chemistry
DatePublished - Aug 2007
Issue number22
Number of pages9
Pages (from-to)3698-3706
Original languageEnglish

Abstract

Two stereoselective syntheses of the octahydropyrano[2,3-b]pyridine DE hemiaminal core of the macrocyclic alkaloid 'upenamide are described. The syntheses proceeded through an efficient stannous chloride-induced deacetalisation-cyclisation procedure. The aza-annulation was stereoselective affording a single stereoisomer having the same relative configuration as in the natural product. The cis ring junction and the cis relationship between 2-H and 8a-H were established by NMR spectroscopy and confirmed by X-ray crystallography. An asymmetric synthesis of the octahydropyrano[2,3-b]pyridine ring system is also disclosed. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

    Research areas

  • 'Upenamide, hemiaminal, stannous chloride, deacetalisation-cyclisation process, aza-annulation, RING-SYSTEM

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