Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling

M S Jensen; C Yang; Y Hsiao; N Rivera; K M Wells; J Y Chung; N Yasuda; D L Hughes; P J Reider

doi:10.1021/ol005641d

Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling

Org Lett. 2000 Apr 20;2(8):1081-4. doi: 10.1021/ol005641d.

Authors

M S Jensen¹, C Yang, Y Hsiao, N Rivera, K M Wells, J Y Chung, N Yasuda, D L Hughes, P J Reider

Affiliation

¹ Department of Process Research, Merck Research Laboratories, Rahway, New Jersey 07065, USA. mark_jensen@merck.com

PMID: 10804559
DOI: 10.1021/ol005641d

Abstract

[formula: see text] A short synthesis of carbapenem 1 is described. They key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemistry*
Carbapenems / chemical synthesis*
Methicillin Resistance*
Organotin Compounds / chemistry*
Staphylococcus aureus / drug effects*

Substances

1-stanna-5-azabicyclo(3.3.3)undecane
Bridged Bicyclo Compounds
Carbapenems
Organotin Compounds