Mark S. Jensen

Preparation of crystallinep-nitrobenzyl 2-hydroxymethyl carbapenem as a key intermediate for the anti-MRS carbapenem L-786,392

Abstract Crystalline p -nitrobenzyl esters of 2-hydroxymethyl carbapenem derivatives were prepared in one pot from the corresponding diazo compounds and Bu 3 SnCH 2 OH. The TES protected 2-hydroxymethyl carbapenem was successfully converted to an anti-MRS carbapenem L-786,392.

A simple and scalable method to prepare 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane

Abstract A simple and scalable method for the preparation of a potentially versatile organostannane, 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane ( 1 ), is described. Stannane 1 was prepared by the disproportionation of N(CH 2 CH 2 CH 2 SnBu 3 ) 3 and SnCl 4 at 70–100°C. This reaction requires the addition of water or an alcohol to proceed efficiently. Under typical conditions, 1 was isolated in 50–55% yield after a simple acid/base extraction sequence.

Preparation of crystalline P-nitrobenzyl 2-formyl carbapenems by oxidative cleavage

Crystalline 1beta-methyl-2-formyl carbapenem pNB esters were prepared by osmium-mediated oxidative cleavage of the corresponding 2-vinyl derivatives. Reduction of the 2-formyl compounds gave the corresponding 2-hydroxymethyl derivatives, which are key intermediates for the anti-MRS carbapenem candidate (1).