Merck + Co., Inc.

Robert K Anderson

Anthony O King

Sander G Mills

Ralph P Volante

Leonard M Weinstock

Richard F Shuman

Ann E DeCamp

Alan T Kawaguchi

Richard E Shuman

This invention discloses novel intermediates and novel process for their preparation where said intermediates are useful for the preparation of 5-oxygenated derivatives (T) of lovastatin and analogs thereof at the 8-acyl side chain and 6-position of the polyhydronaphthyl ring. Said derivatives of lovastatin (T) and analogs thereof are useful in treating hypercholesterolemia and are disclosed in the U.S. Pat. No. 4,963,538. ##STR1##

Processes and intermediates for the preparation of 5-oxygenated HMG-CoA

A process utilizes the tetrazole functional group to direct lithiation at the ortho position of a phenyltetrazole and generate a nucleophilic aryllithium species which then undergoes reaction with an electrophile to generate a 2-substituted 1-(tetrazol-5-yl)benzene. The process is useful in the production of intermediates in the synthesis of angiotensin II antagonists. This novel process is a more cost effective and versatile route for the large-scale preparation of these key intermediates.

Ortho-lithiation process for the synthesis of 2-substituted

A process for introducing a 1,2 double bond into a compound of the formula ##STR1## which comprises the process of (a) treating the compound of formula I with oxalyl chloride; (b) brominating the product of step (a) followed by in situ dehydrobromination; (c) deprotecting the product of step (b) to yield the .alpha. and .beta. isomers; (d) dehydrobrominating the product of step (c), which results in the introduction of a double bond at the 1,2 position.

Method for introducing a 1,2 double bond into azasteroids

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Plainsboro, NJ, United States of America

Robert K Anderson