Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues?

RSC Advances Pub Date: 2014-08-18 DOI: 10.1039/C4RA05981F

Abstract

A facile and efficient synthetic method for the stereoselective preparation of trisubstituted tetrahydro-β-carboline-fused diketopiperazine derivatives is reported. The methodology represents a one-pot four-step reaction, employing the Ugi four-component condensation which is followed by a Boc-deprotection, a Pictet–Spengler reaction and a final lactamization. All THBC-DKPs were obtained in good yields and excellent diastereomeric excess.

Graphical abstract: Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues
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