Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.

Original languageEnglish
Pages (from-to)11340-11343
Number of pages4
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume21
Issue number32
DOIs
Publication statusPublished - 2015 Aug 3

Fingerprint

Asparagine
Tryptophan
Chemical activation
Derivatives
Amination
Acids
Amino acids
Amino Acids
clavicipitic acid

Keywords

  • 4-substituted tryptophan derivatives
  • clavicipitic acid
  • CH activation
  • iridium
  • total synthesis

ASJC Scopus subject areas

  • Medicine(all)

Cite this

@article{d48d6d90575b4ef5b8724f8ac8919e04,
title = "Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step",
abstract = "4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.",
keywords = "4-substituted tryptophan derivatives, clavicipitic acid, CH activation, iridium, total synthesis",
author = "Tahara, {Yu Ki} and Mamoru Ito and Kanyiva, {Stephen Kyalo} and Takanori Shibata",
year = "2015",
month = "8",
day = "3",
doi = "10.1002/chem.201502300",
language = "English",
volume = "21",
pages = "11340--11343",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "32",

}

TY - JOUR

T1 - Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step

AU - Tahara, Yu Ki

AU - Ito, Mamoru

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

PY - 2015/8/3

Y1 - 2015/8/3

N2 - 4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.

AB - 4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.

KW - 4-substituted tryptophan derivatives

KW - clavicipitic acid

KW - CH activation

KW - iridium

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84965184027&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84965184027&partnerID=8YFLogxK

U2 - 10.1002/chem.201502300

DO - 10.1002/chem.201502300

M3 - Article

C2 - 26178075

AN - SCOPUS:84937684742

VL - 21

SP - 11340

EP - 11343

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 32

ER -