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Abstract: A rapid access to jaspine B and its enantiomer ent-jaspine B from a 2,3-aziridino-γ-lactone is reported. This synthesis relies on a one pot regioselective aziridine ring-opening followed by intramolecular cyclization to install the cis-amino–alcohol pattern of jaspine B and on a modified Julia olefination of the lactone followed by a diastereoselective hydrogenation for the introduction of the C14 aliphatic chain. The separation of enantiomers in the course of this synthesis was achieved by supercritical fluid chromatography. The cytotoxicity of both enantiomers was evaluated. [Copyright &y& Elsevier]

Abstract: An improved divergent synthesis of the four diastereomers of pachastrissamine from Garner's aldehyde has been reported. The common intermediate was synthesized by an indium-mediated acetoxyallylation reaction. The long alkyl side chain was introduced in the late stage of the synthesis using an olefin cross metathesis reaction. Biological evaluation of the chain modified analogs of the (2S,3S,4R)-isomer demonstrated that biological activity was highly dependent on the chain length. [Copyright &y& Elsevier]