Preparation of renieramycin left-half model compounds

Keiyou Nakai, Keiji Kubo, Masashi Yokoya, Naoki Saito

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Model compounds of the left-half of renieramycins, which are anticancer marine natural products having an α-aminonitrile functionality, were prepared from phenylalanine derivatives. The key step of the transformation is the stereospecific construction of 1,3-cis stereochemistry via an exomethylene intermediate. The stereoselective α-aminonitrile formation under kinetically controlled conditions is also discussed. The initial cytotoxicity profiles are presented.

Original languageEnglish
Pages (from-to)6529-6545
Number of pages17
JournalTetrahedron
Volume70
Issue number37
DOIs
Publication statusPublished - Sep 16 2014
Externally publishedYes

Fingerprint

Stereochemistry
Cytotoxicity
Biological Products
Phenylalanine
Derivatives

Keywords

  • Cytotoxicity
  • Isoquinoline
  • Marine natural product
  • Preparation
  • Renieramycin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Nakai, K., Kubo, K., Yokoya, M., & Saito, N. (2014). Preparation of renieramycin left-half model compounds. Tetrahedron, 70(37), 6529-6545. https://doi.org/10.1016/j.tet.2014.07.012

Preparation of renieramycin left-half model compounds. / Nakai, Keiyou; Kubo, Keiji; Yokoya, Masashi; Saito, Naoki.

In: Tetrahedron, Vol. 70, No. 37, 16.09.2014, p. 6529-6545.

Research output: Contribution to journalArticle

Nakai, K, Kubo, K, Yokoya, M & Saito, N 2014, 'Preparation of renieramycin left-half model compounds', Tetrahedron, vol. 70, no. 37, pp. 6529-6545. https://doi.org/10.1016/j.tet.2014.07.012
Nakai K, Kubo K, Yokoya M, Saito N. Preparation of renieramycin left-half model compounds. Tetrahedron. 2014 Sep 16;70(37):6529-6545. https://doi.org/10.1016/j.tet.2014.07.012
Nakai, Keiyou ; Kubo, Keiji ; Yokoya, Masashi ; Saito, Naoki. / Preparation of renieramycin left-half model compounds. In: Tetrahedron. 2014 ; Vol. 70, No. 37. pp. 6529-6545.
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