Add time:07/29/2019 Source:sciencedirect.com
The reaction between 6-acetyl-3-alkyl-1-ethoxy-3,4,5a,6,11,11a-hexahydro-10bH-pyrazino-[2′,1′-5,1]pyrrolo[2,3-b]indole-1,4-diones and anthranilic acid was studied from a stereochemical point of view. Various degrees of epimerization of the tryptophan and alanine stereocenters were observed in compounds with a cis relationship between their H-3 and H-11a hydrogen atoms, and stereochemistry was retained in the trans compounds. These observations are explained in terms of steric compression between the C5O, C7–alkyl and C8O groups in the hexacyclic reaction products. Acylation at N-2 with o-azidobenzoyl chloride followed by an intramolecular aza Wittig reaction afforded the target 10-acetyl-5,7,8,9a,10,14b,15,15a-octahydroindolo[3″,2″-4′,5′]pyrrolo[2′,1′-3,4]pyrazino[2,1-b]quinazoline-5,8-diones with retention of all stereocenters.
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