Helvetica Chimica Acta p. 1653 - 1670 (1991)
Update date:2022-09-26
Topics:
Defoin, Albert
Pires, Joaquim
Streith, Jacques
Acylnitroso dienophiles 4 reacted instantly with 1-(silyloxy)butadiene 5α and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table 1). cis-Hydroxylation of these primary cycloadducts with OsO4 (catalyst) occurred stereospecifically and in high yield (-> 8 and 9, resp.: Scheme 2).It was followed by reductive ring cleavage to give either 1-amino-1-deoxy-DL-erythriol or 4-amino-4-deoxy-DL-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4).
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