Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin

Masaya Nakata, Seiji Akazawa, Shuji Kitamura, Kuniaki Tatsuta

Research output: Contribution to journal › Article

59 Citations (Scopus)

Abstract

Total synthesis of (-)-allosamizoline (2), an aminocyclitol moiety of the insect chitinase inhibitor allosamidin (1) has been enantiospecifically synthesized from D-glucosamine by using an intramolecular cycloaddition of the nitrile oxide to an olefin as a key step.

Original languageEnglish
Pages (from-to)5363-5366
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number39
DOIs
Publication statusPublished - 1991 Sep 23

Fingerprint

allosamidin
Chitinases
Nitriles
Cycloaddition
Glucosamine
Cycloaddition Reaction
Alkenes
Oxides
Insects
allosamizoline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin. / Nakata, Masaya; Akazawa, Seiji; Kitamura, Shuji; Tatsuta, Kuniaki.

In: Tetrahedron Letters, Vol. 32, No. 39, 23.09.1991, p. 5363-5366.

Research output: Contribution to journal › Article

Nakata, M, Akazawa, S, Kitamura, S & Tatsuta, K 1991, 'Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin', Tetrahedron Letters, vol. 32, no. 39, pp. 5363-5366. https://doi.org/10.1016/S0040-4039(00)92386-4
Nakata M, Akazawa S, Kitamura S, Tatsuta K. Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin. Tetrahedron Letters. 1991 Sep 23;32(39):5363-5366. https://doi.org/10.1016/S0040-4039(00)92386-4
Nakata, Masaya ; Akazawa, Seiji ; Kitamura, Shuji ; Tatsuta, Kuniaki. / Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 39. pp. 5363-5366.
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