Helvetica chimica acta

Syntheses of Amino??dideoxyallose and Amino??deoxyribose Derivatives Using Acylnitroso Dienophiles

A Defoin, H Fritz, G Geffroy, J Streith

Index: Defoin, Albert; Fritz, Hans; Geffroy, Guillaume; Streith, Jacques Helvetica Chimica Acta, 1988 , vol. 71, p. 1642 - 1658

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Citation Number: 25

Abstract

Abstract The dimethyl acetals 4 of (E)-2, 4-pentadienal and of (E, E)-and (E, Z)-2, 4- hexadienals undergo regio-and stereospecific cycloaddition reactions with in-situ-generated acylnitroso dienophiles 5a and 5b, leading thereby to the corresponding dihydrooxazines 7a– d and 8c–d. cis-Glycolization of these latter adducts stereospecifically gave the dihydro derivatives 9a–d and 10d which, after sequential hydrogenolysis, deacetalization, and ...

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