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Biomimetic synthesis of bis-alpha-substituent pyrrolidine alkaloids based on a proposed biosynthetic pathway

Release Time:2019-03-13  Hits:

Indexed by: Journal Article

Date of Publication: 2016-05-25

Journal: TETRAHEDRON LETTERS

Included Journals: Scopus、SCIE

Volume: 57

Issue: 21

Page Number: 2219-2221

ISSN: 0040-4039

Key Words: Bis-alpha-substituent pyrrolidine alkaloids; Pyrroloxazine alkaloids; Pyrrolozoxazine; Biosynthetic pathway

Abstract: A possible biosynthetic pathway of bis-alpha-substituent pyrrolidine alkaloids was proposed. Based on the proposed biosynthetic pathway, six pyrrolozoxazine alkaloids and one N-alkyl-5-hydroxymethyl-pyr-role-2-carbaldehyde alkaloid were synthesized. In a mixture of acetic acid and triethylamine, condensation of n-fructose and D-amino acids produced pyrrolozoxazine alkaloids. Replacing D-amino acids with tyramine can afford pyrrolezanthine a N-alkyl-5-hydroxymethyl-pyr-role-2-carbaldehyde alkaloid. (C) 2016 Published by Elsevier Ltd.

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