Stereoselective Synthesis of 1-Aminocyclopropanecarboxylic Acid Carnosadines via Inter-intramolecular Double Alkylation with Optically Active 2-Methylaziridine Derivatives

Kosuke Ohsawa, Junya Kubota, Shota Ochiai, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

Abstract

The stereoselective and short-step synthesis of N-protected allo-carnosadine, ent-carnosadine, and carnosadine lactam was accomplished from a common cyclopropane intermediate. The inter-intramolecular double alkylation of diethyl malonate with an optically active 2-methylaziridine derivative gave the key cyclopropane in excellent yield and optical purity. The following monohydrolysis of the diester moiety using different reaction conditions provided both diastereomers of monoacids, which were converted to three carnosadine derivatives in 5-6 steps from the common diester.

Original languageEnglish
Pages (from-to)7304-7313
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number10
DOIs
Publication statusPublished - 2021 May 21

ASJC Scopus subject areas

  • Organic Chemistry

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