Nine-step enantioselective total synthesis of (+)-minfiensine.

نویسندگان

  • Spencer B Jones
  • Bryon Simmons
  • David W C MacMillan
چکیده

An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

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Efficient syntheses of (–)-crinine and (–)-aspidospermidine, and the formal synthesis of (–)-minfiensine by enantioselective intramolecular dearomative cyclization† †Electronic supplementary information (ESI) available. CCDC 1444649 and 1537084. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01859b Click here for additional data file. Click here for additional data file.

Kang Du, He Yang, Pan Guo, a,+ Liang Feng, Guangqing Xu, Qinghai Zhou, Lung Wa Chung and Wenjun Tang* a State Key Laboratory of Bio-Organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences b Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China c College of Chemistry, Nankai University...

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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 131 38  شماره 

صفحات  -

تاریخ انتشار 2009