Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis

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• 作者：Yuji Yoshimitsu ; Jun Miyagaki ; Shinya Oishi ; Nobutaka Fujii ; ^{nfujii@pharm.kyoto-u.ac.jp} ; Hiroaki Ohno ; ^{hohno@pharm.kyoto-u.ac.jp}
• 关键词：Pachastrissamine ; Jaspine B ; Divergent synthesis ; Olefin cross metathesis
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：27 May, 2013
• 年：2013
• 卷：69
• 期：21
• 页码：4211-4220
• 全文大小：742 K

文摘

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.