Literature DB >> 21132176

Efficient total synthesis of (-)-stemoamide.

Toshio Honda1, Tomoha Matsukawa, Kazunori Takahashi.   

Abstract

An efficient diastereoselective synthesis of (-)-stemoamide has been accomplished from a pyroglutamic acid derivative in eight steps and with 24% overall yield. The synthesis features an intramolecular samarium diiodide-promoted 7-exo-trig cyclization of a ketyl radical generated from the corresponding aldehyde.

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Year:  2010        PMID： 21132176     DOI： 10.1039/c0ob00850h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  3 in total

1.  Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

Authors:  Adam T Hoye; Peter Wipf
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

2.  Pyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A.

Authors:  Xianglin Yin; Kaiqing Ma; Ying Dong; Mingji Dai
Journal:  Org Lett       Date:  2020-06-17       Impact factor: 6.005

3.  Recent advances in the chemistry of ketyl radicals.

Authors:  Áron Péter; Soumitra Agasti; Oliver Knowles; Emma Pye; David J Procter
Journal:  Chem Soc Rev       Date:  2021-03-23       Impact factor: 54.564
  3 in total

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