Synthetic studies on the thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dehydropiperidine and piperidine cores

Syuhei Higashibayashi; Kimiko Hashimoto; Masaya Nakata

doi:10.1016/S0040-4039(01)02090-1

Synthetic studies on the thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dehydropiperidine and piperidine cores

Syuhei Higashibayashi, Kimiko Hashimoto, Masaya Nakata

School of Pharmaceutical Sciences

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

28 Citations (Scopus)

Abstract

The tetrasubstituted dehydropiperidine and piperidine cores of the thiostrepton family of peptide antibiotics were synthesized which featured the coupling between the azomethine ylide and the enantiopure sulfinimine, and the subsequent stereoselective reduction of the six-membered imine.

Original language	English
Pages (from-to)	105-110
Number of pages	6
Journal	Tetrahedron Letters
Volume	43
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4039(01)02090-1
Publication status	Published - 2002 Jan 1

Keywords

Piperidines
Stereoselective reduction
Sulfinimines
Thiostrepton

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(01)02090-1

Cite this

@article{f984e21291b14c56b853273e2374aa04,

title = "Synthetic studies on the thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dehydropiperidine and piperidine cores",

abstract = "The tetrasubstituted dehydropiperidine and piperidine cores of the thiostrepton family of peptide antibiotics were synthesized which featured the coupling between the azomethine ylide and the enantiopure sulfinimine, and the subsequent stereoselective reduction of the six-membered imine.",

keywords = "Piperidines, Stereoselective reduction, Sulfinimines, Thiostrepton",

author = "Syuhei Higashibayashi and Kimiko Hashimoto and Masaya Nakata",

note = "Funding Information: This research was supported by a Grant-in Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Exploitation of Multi-Element Cyclic Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2002",

month = jan,

day = "1",

doi = "10.1016/S0040-4039(01)02090-1",

language = "English",

volume = "43",

pages = "105--110",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - Synthetic studies on the thiostrepton family of peptide antibiotics

T2 - Synthesis of the tetrasubstituted dehydropiperidine and piperidine cores

AU - Higashibayashi, Syuhei

AU - Hashimoto, Kimiko

AU - Nakata, Masaya

N1 - Funding Information: This research was supported by a Grant-in Aid for Scientific Research on Priority Areas (A) ‘Exploitation of Multi-Element Cyclic Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2002/1/1

Y1 - 2002/1/1

N2 - The tetrasubstituted dehydropiperidine and piperidine cores of the thiostrepton family of peptide antibiotics were synthesized which featured the coupling between the azomethine ylide and the enantiopure sulfinimine, and the subsequent stereoselective reduction of the six-membered imine.

AB - The tetrasubstituted dehydropiperidine and piperidine cores of the thiostrepton family of peptide antibiotics were synthesized which featured the coupling between the azomethine ylide and the enantiopure sulfinimine, and the subsequent stereoselective reduction of the six-membered imine.

KW - Piperidines

KW - Stereoselective reduction

KW - Sulfinimines

KW - Thiostrepton

UR - http://www.scopus.com/inward/record.url?scp=0036134113&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036134113&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)02090-1

DO - 10.1016/S0040-4039(01)02090-1

M3 - Article

AN - SCOPUS:0036134113

VL - 43

SP - 105

EP - 110

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 1

ER -

Synthetic studies on the thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dehydropiperidine and piperidine cores

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this