A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization.

نویسندگان

  • Hao Liu
  • Ruijiao Chen
  • Xiaochuan Chen
چکیده

A flexible and practical protocol for the asymmetric synthesis of renieramycin-type antitumor alkaloids is described, in which the stereoselective Pictet-Spengler cyclization of amino ester 16 and aldehyde 15 by regulating temperature and the automatic lactamization after N-deprotection of the cyclization product are exploited to rapidly construct the common pentacyclic framework. (-)-Renieramycin G and (-)-jorunnamycin A, as representative members of the two subgroup renieramycin-type alkaloids, are obtained in 19 steps from l-tyrosine with 15.8% and 14.3% overall yield respectively.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 12 10  شماره 

صفحات  -

تاریخ انتشار 2014