Isoxazolinyl Spironucleosides: Stereoselectivity of 1,3-Dipolar Cycloadditions of 7-Methylenepyrrolo[1,2-c]pyrimidin-1(5H)-ones

Abstract Novel 7-methylenepyrrolo[1,2-C]pyrimidin-1(5H)-ones 11A-C were synthesized from commercially available orotic acid (6). 1,3-Dipolar cycloadditions of mesitonitrile oxide to the exocyclic double bond of the dipolarophiles 11 proceed with complete regioselectivity and lead to the spiroisoxazo...

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Published in:Synlett 2003-12, Vol.2003 (15), p.2364-2368
Main Authors: Fischer, Róbert, Hýrošová, Eva, Drucková, Alexandra, Fišera, Lubor, Hametner, Christian, Cyrański, Michał K.
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container_issue 15
container_start_page 2364
container_title Synlett
container_volume 2003
creator Fischer, Róbert
Hýrošová, Eva
Drucková, Alexandra
Fišera, Lubor
Hametner, Christian
Cyrański, Michał K.
description Abstract Novel 7-methylenepyrrolo[1,2-C]pyrimidin-1(5H)-ones 11A-C were synthesized from commercially available orotic acid (6). 1,3-Dipolar cycloadditions of mesitonitrile oxide to the exocyclic double bond of the dipolarophiles 11 proceed with complete regioselectivity and lead to the spiroisoxazolinyl nucleosides 13 and 14 in good yields. Attack of the dipole from the less sterically hindered side of the dipolarophile affords C-5/C-7 TRANS isoxazolines as major isomers predominantly. The protection of the free hydroxyl group by the bulky substituent (TBDPS) leads to formation C-5/C-7 TRANS isomer 14C exclusively.
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title Isoxazolinyl Spironucleosides: Stereoselectivity of 1,3-Dipolar Cycloadditions of 7-Methylenepyrrolo[1,2-c]pyrimidin-1(5H)-ones
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