Synthesis of 3-alkenyl-Δ2-cephems by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem with alkenyltributyltins

Hideo Tanaka, Shin Ichi Sumida, Sigeru Torii

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Synthesis of 3-alkenyl-Δ2-cephems 3 was performed in regioselective by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem 1 with alkenyltributyltins. Subsequent Diels-Alder reaction of the 3-vinyl-Δ2-cephem 3a with acrolein opened a new access to C(2)-C(3) fused tricyclic cephalosporin 9.

Original languageEnglish
Pages (from-to)5967-5970
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number33
DOIs
Publication statusPublished - Aug 12 1996

Fingerprint

Alkenylation
Acrolein
Cycloaddition Reaction
Cephalosporins
cuprous chloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 3-alkenyl-Δ2-cephems by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem with alkenyltributyltins. / Tanaka, Hideo; Sumida, Shin Ichi; Torii, Sigeru.

In: Tetrahedron Letters, Vol. 37, No. 33, 12.08.1996, p. 5967-5970.

Research output: Contribution to journalArticle

@article{74dce2b7504c4e5c927fda2a8c7cac2b,
title = "Synthesis of 3-alkenyl-Δ2-cephems by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem with alkenyltributyltins",
abstract = "Synthesis of 3-alkenyl-Δ2-cephems 3 was performed in regioselective by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem 1 with alkenyltributyltins. Subsequent Diels-Alder reaction of the 3-vinyl-Δ2-cephem 3a with acrolein opened a new access to C(2)-C(3) fused tricyclic cephalosporin 9.",
author = "Hideo Tanaka and Sumida, {Shin Ichi} and Sigeru Torii",
year = "1996",
month = "8",
day = "12",
doi = "10.1016/0040-4039(96)01289-0",
language = "English",
volume = "37",
pages = "5967--5970",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "33",

}

TY - JOUR

T1 - Synthesis of 3-alkenyl-Δ2-cephems by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem with alkenyltributyltins

AU - Tanaka, Hideo

AU - Sumida, Shin Ichi

AU - Torii, Sigeru

PY - 1996/8/12

Y1 - 1996/8/12

N2 - Synthesis of 3-alkenyl-Δ2-cephems 3 was performed in regioselective by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem 1 with alkenyltributyltins. Subsequent Diels-Alder reaction of the 3-vinyl-Δ2-cephem 3a with acrolein opened a new access to C(2)-C(3) fused tricyclic cephalosporin 9.

AB - Synthesis of 3-alkenyl-Δ2-cephems 3 was performed in regioselective by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Δ3-cephem 1 with alkenyltributyltins. Subsequent Diels-Alder reaction of the 3-vinyl-Δ2-cephem 3a with acrolein opened a new access to C(2)-C(3) fused tricyclic cephalosporin 9.

UR - http://www.scopus.com/inward/record.url?scp=0030581395&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030581395&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(96)01289-0

DO - 10.1016/0040-4039(96)01289-0

M3 - Article

AN - SCOPUS:0030581395

VL - 37

SP - 5967

EP - 5970

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 33

ER -