73 STUDIES ON A NEW SYNTHESIS OF THE ACYCLIC AMIDE AND MACROCYCLIC LACTAM ALKALOIDS

DOI
  • Nagao Y.
    Institute for Chemical Research, Kyoto University
  • Seno K.
    Institute for Chemical Research, Kyoto University
  • Miyasaka T.
    Institute for Chemical Research, Kyoto University
  • Kawabata K.
    Institute for Chemical Research, Kyoto University
  • Takao S.
    Institute for Chemical Research, Kyoto University
  • Fujita E.
    Institute for Chemical Research, Kyoto University

Bibliographic Information

Other Title
  • 73 非環状アミドアルカロイドならびに大環状ラクタムアルカロイドの新合成研究

Abstract

An efficiently monitored aminolysis of 3-acylthiazolidine-2-thione (1) has been found to give a very high yield of amide (6). Experimental results are shown in Table 2. The similar aminolysis of 3-hexadecanoylthiazolidine-2-thione (1c) with many kinds of aminoalcohols resulted in the chemospecific formation of the desired hydroxyamides in satisfactory yields. (See Table 3.) Subsequently, naturally occurring amide alkaloids, fagaramide (14), dolichotheline (16), and maytenine (18) were synthesized in good yields by the application of the foregoing aminolysis. Synthesis of macrocyclic lactams was also successfully carried out. (See Table 4.) The total synthesis of codonocarpine (37), a macrocyclic spermidine alkaloid,utilizing this aminolysis as a key step is now in progress.

Journal

Details 詳細情報について

  • CRID
    1390282681049381760
  • NII Article ID
    110006678100
  • DOI
    10.24496/tennenyuki.22.0_554
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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