Synthesis of 9-substituted tetrahydrodiazepinopurines: Studies toward the total synthesis of asmarines

Doron Pappo, Shiri Shimony, Yoel Kashman

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

(Chemical Equation Presented). A methodology for the preparation of asmarine analogues has been developed. The asmarines are cytotoxic marine alkaloids with a unique tetrahydro[1,4]diazepino[1,2,3-g,h]purine (THDAP) structure. Three cyclization methods were applied for the preparation of the 9,9-disubstituted 10-hydroxy-THDAP system, namely, aminomercurization, iodocyclization, and acid-catalyzed cyclization. The DMPM group of the NOH functionality and cyanoethyl group of the N-9 atom were found to be the most suitable protecting groups. The structures of all compounds were mainly determined from NMR measurements including 15N chemical shifts obtained from 15NH HMBC spectra. The end products are at least about 1 order of magnitude less active than the natural product asmarine B.

Original languageEnglish
Pages (from-to)199-206
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number1
DOIs
StatePublished - 7 Jan 2005
Externally publishedYes

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