Regio- and stereoselective synthesis of N-H aziridines by N-N bond reduction of N-quinazolinyl aziridines

Hydroxyl-directed aziridination of the isoprenoid alcohols - geraniol, nerol, and (E,E)-farnesol - with Atkinson's N-acetoxyamino-2-ethyl-4(3H)-quinazolone reagent (4) afforded N-substituted 2,3-epimino alcohols. Reduction of these and related N-substituted aziridines with metal-ammonia or lith...

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Bibliographic Details
Published inTetrahedron Vol. 55; no. 32; pp. 9669 - 9686
Main Authors Koohang, A, Stanchina, CL, Coates, RM
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 06.08.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
aziridines
STEROLS
SQUALENE
CLEAVAGE
SACCHAROMYCES-CEREVISIAE
polyenols
ALKENES
BIOSYNTHESIS
ESTERS
INHIBITORS
reduction
quinazolinones
DERIVATIVES
CYCLIZATION
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Summary:Hydroxyl-directed aziridination of the isoprenoid alcohols - geraniol, nerol, and (E,E)-farnesol - with Atkinson's N-acetoxyamino-2-ethyl-4(3H)-quinazolone reagent (4) afforded N-substituted 2,3-epimino alcohols. Reduction of these and related N-substituted aziridines with metal-ammonia or lithium-naphthalenide reagents furnished a series of N-H aziridino alcohols (53-74%) including 2,3- and 6,7-epimino geraniols (10 and 13), 2,3-epimino nerol (17), (E,E)-2,3-epimino farnesol (23), and syn-2,3-epimino isophorol (20). A less efficient synthesis of the trans-2,3-epimino isoprenoid alcohols 10 and 23 by irradiation of allylic azidoformates and hydrolysis of the oxazolidinone photoproducts is also reported. These approaches complement known methods for synthesis of N-H aziridines of isoprenoid polyenes. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(99)00522-0