FROM 1-(SILYLOXY)BUTADIENE TO 4-AMINO-4-DEOXY-DL-ERYTHROSE AND TO 1-AMINO-1-DEOXY-DL-ERYTHRITOL DERIVATIVES VIA HETERO-DIELS-ALDER REACTIONS WITH ACYLNITROSO DIENOPHILES

Acylnitroso dienophiles 4 reacted instantly with 1-(silyloxy)butadiene 5-alpha 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-erythritol or 4-amino-4-deoxy-DL-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4).