Preparation of renieramycin left-half model compounds

Keiyo Nakai; Keiji Kubo; Masashi Yokoya; Naoki Saito

doi:10.1016/j.tet.2014.07.012

Preparation of renieramycin left-half model compounds

Keiyo Nakai, Keiji Kubo, Masashi Yokoya, Naoki Saito

Graduate School of Medicine Dentistry and Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	6529-6545
Number of pages	17
Journal	Tetrahedron
Volume	70
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2014.07.012
Publication status	Published - Sept 16 2014

Keywords

Cytotoxicity
Isoquinoline
Marine natural product
Preparation
Renieramycin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.tet.2014.07.012

Cite this

@article{ced01b1704ac4e34b46a93a496151d4e,

title = "Preparation of renieramycin left-half model compounds",

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.",

keywords = "Cytotoxicity, Isoquinoline, Marine natural product, Preparation, Renieramycin",

author = "Keiyo Nakai and Keiji Kubo and Masashi Yokoya and Naoki Saito",

year = "2014",

month = sep,

day = "16",

doi = "10.1016/j.tet.2014.07.012",

language = "English",

volume = "70",

pages = "6529--6545",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - Preparation of renieramycin left-half model compounds

AU - Nakai, Keiyo

AU - Kubo, Keiji

AU - Yokoya, Masashi

AU - Saito, Naoki

PY - 2014/9/16

Y1 - 2014/9/16

N2 - 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.

AB - 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.

KW - Cytotoxicity

KW - Isoquinoline

KW - Marine natural product

KW - Preparation

KW - Renieramycin

UR - http://www.scopus.com/inward/record.url?scp=84949116031&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84949116031&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.07.012

DO - 10.1016/j.tet.2014.07.012

M3 - Article

AN - SCOPUS:84949116031

SN - 0040-4020

VL - 70

SP - 6529

EP - 6545

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Preparation of renieramycin left-half model compounds

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this