Total synthesis of (+)-yatakemycin

Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama

doi:10.1021/ja0619455

Total synthesis of (+)-yatakemycin

Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

PHA - Molecular Pharmaceutical Science

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

108 Citations (Scopus)

Abstract

A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl₃ in the presence of pentamethylbenzene.

Original language	English
Pages (from-to)	7136-7137
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	22
DOIs	https://doi.org/10.1021/ja0619455
Publication status	Published - 2006 Jun 7

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja0619455

Cite this

@article{e51dacfcedba42658410768af342328f,

title = "Total synthesis of (+)-yatakemycin",

abstract = "A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.",

author = "Kentaro Okano and Hidetoshi Tokuyama and Tohru Fukuyama",

year = "2006",

month = jun,

day = "7",

doi = "10.1021/ja0619455",

language = "English",

volume = "128",

pages = "7136--7137",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Total synthesis of (+)-yatakemycin

AU - Okano, Kentaro

AU - Tokuyama, Hidetoshi

AU - Fukuyama, Tohru

PY - 2006/6/7

Y1 - 2006/6/7

N2 - A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.

AB - A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.

UR - http://www.scopus.com/inward/record.url?scp=33744928097&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744928097&partnerID=8YFLogxK

U2 - 10.1021/ja0619455

DO - 10.1021/ja0619455

M3 - Article

C2 - 16734447

AN - SCOPUS:33744928097

SN - 0002-7863

VL - 128

SP - 7136

EP - 7137

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 22

ER -

Total synthesis of (+)-yatakemycin

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this