Direct Conversion of N-Alkoxy β-Lactams to Carbapenams: Application to the Synthesis of the Bicyclic PS-5 Keto Ester

DOI: 10.1021/jo00008a022

Source and publish data:

Journal of Organic Chemistry p. 2688 - 2694 (1991)

Update date:2022-08-04

Topics:

Authors:

Williams, Matthew A.

Hsiao, Chi-Nung

Miller, Marvin J.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1021/jo00008a022

The synthesis and direct conversion of N-alkoxy β-lactams to the carbapenam ring system is described.This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement.The title reaction is applied to the construction of the methyl ester of the bicyclic β-lactam precursor of PS-5.

Full text of DOI:10.1021/jo00008a022

Products guided by the article

Product name:methyl 4-<1-(benzyloxy)-2-oxo-3(S)-ethyl-4(R)-azetidinyl>-β-ketobutyrate

Cas No:133374-73-9

R&D Labs maybe for 133374-73-9

Hebei Tianxiang Biological & Pharmaceutical Co., Ltd

Contact:86-0312-6615158

Address:No 42 fazhan street qingyuan county
Qingdao XinYongAn Chemicals Co., Ltd

Contact:+86-532-81107967

Address:Chengyang dual-port industrial park by the sea，Qingdao
Anhui Asahikasei Chemical Co., Ltd

Contact:86-551-4259770

Address:No. 88 Linquan Road Hefei Anhui China
wuxi huabin bio-tech Co.,Ltd(expird)

Contact:86-0510-85133006

Address:hubin road NO157
Shanghai Demand Chemical Co., ltd，China

Contact:86-021-55237578/55239122

Address:Room 3H, No.578, Yingkou Road, Yangpu District, Shanghai, China

Relevant to this article

Synthesis, Physicochemical and Conformational Properties of (3R,4R)-3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo<2.2.1>heptane, a Novel M₁ Selective Muscarinic Partial Agonist

Doi:10.1039/c39920000817
(1992)
Synthesis of phosphorus isosters of β-amyloid peptides fragments

Doi:10.1134/S1070363215090121
(2015)
Complete stereochemistry of neamphamide A and absolute configuration of the β-methoxytyrosine residue in papuamide B

Doi:10.1021/jo0508853
(2005)
Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

Doi:10.1021/ol0508025
(2005)
Screening for cardiovascular safety: A structure-activity approach for guiding lead selection of melanin concentrating hormone receptor 1 antagonists

Doi:10.1021/jm0512286
(2006)
Microbial transformation of (+)- and (-)-2'-demethoxydehydrogriseofulvin by Streptomyces cinereocrocatus

Doi:10.1248/cpb.31.934
(1983)

Article Doi