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

Yu Ki Tahara; Mamoru Ito; Stephen Kyalo Kanyiva; Takanori Shibata

doi:10.1002/chem.201502300

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

Yu Ki Tahara, Mamoru Ito, Stephen Kyalo Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

33 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 language	English
Pages (from-to)	11340-11343
Number of pages	4
Journal	Chemistry - A European Journal
Volume	21
Issue number	32
DOIs	https://doi.org/10.1002/chem.201502300
Publication status	Published - 2015 Aug 1

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201502300

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, C-H activation, clavicipitic acid, iridium, total synthesis",

author = "Tahara, {Yu Ki} and Mamoru Ito and Kanyiva, {Stephen Kyalo} and Takanori Shibata",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = aug,

day = "1",

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 - 2015/8/1

Y1 - 2015/8/1

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 - C-H activation

KW - clavicipitic acid

KW - iridium

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84937684742&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84937684742&partnerID=8YFLogxK

U2 - 10.1002/chem.201502300

DO - 10.1002/chem.201502300

M3 - Article

C2 - 26178075

AN - SCOPUS:84937684742

SN - 0947-6539

VL - 21

SP - 11340

EP - 11343

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 32

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this