Synthesis of 3-alkenyl-Δ3-cephems via sequential reductive 1,2- elimination/ addition/cyclization in an alkenyltin/copper(I) chloride/bpy system

Hideo Tanaka; Yoshihisa Tokumaru; Sigeru Torii

doi:10.1055/s-1999-2735

Synthesis of 3-alkenyl-Δ³-cephems via sequential reductive 1,2- elimination/ addition/cyclization in an alkenyltin/copper(I) chloride/bpy system

Hideo Tanaka, Yoshihisa Tokumaru, Sigeru Torii

Faculty of Engineering

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

6 Citations (Scopus)

Abstract

A sequential reductive 1,2-elimination-addition-cyclization of 3,4- disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2'-bipyridine (bpy) in N- methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ³-cephems.

Original language	English
Pages (from-to)	774-776
Number of pages	3
Journal	Synlett
Issue number	6
DOIs	https://doi.org/10.1055/s-1999-2735
Publication status	Published - Jan 1 1999

Keywords

3,4-disubstituted butenoate
3-alkeyl-Δ-cephems
Addition/cyclization
Alkenyltin/CuCl system
Reductive 1,2- elimination

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-1999-2735

Cite this

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title = "Synthesis of 3-alkenyl-Δ3-cephems via sequential reductive 1,2- elimination/ addition/cyclization in an alkenyltin/copper(I) chloride/bpy system",

abstract = "A sequential reductive 1,2-elimination-addition-cyclization of 3,4- disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2'-bipyridine (bpy) in N- methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ3-cephems.",

keywords = "3,4-disubstituted butenoate, 3-alkeyl-Δ-cephems, Addition/cyclization, Alkenyltin/CuCl system, Reductive 1,2- elimination",

author = "Hideo Tanaka and Yoshihisa Tokumaru and Sigeru Torii",

year = "1999",

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doi = "10.1055/s-1999-2735",

language = "English",

pages = "774--776",

journal = "Synlett",

issn = "0936-5214",

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T1 - Synthesis of 3-alkenyl-Δ3-cephems via sequential reductive 1,2- elimination/ addition/cyclization in an alkenyltin/copper(I) chloride/bpy system

AU - Tanaka, Hideo

AU - Tokumaru, Yoshihisa

AU - Torii, Sigeru

PY - 1999/1/1

Y1 - 1999/1/1

N2 - A sequential reductive 1,2-elimination-addition-cyclization of 3,4- disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2'-bipyridine (bpy) in N- methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ3-cephems.

AB - A sequential reductive 1,2-elimination-addition-cyclization of 3,4- disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2'-bipyridine (bpy) in N- methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ3-cephems.

KW - 3,4-disubstituted butenoate

KW - 3-alkeyl-Δ-cephems

KW - Addition/cyclization

KW - Alkenyltin/CuCl system

KW - Reductive 1,2- elimination

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