(+ -)-4-AMINO-4,5-DIDEOXYRIBOSE, (+/-)-4-AMINO-4-DEOXYERYTHROSE, AND (+/-)-DIHYDROXYPROLINE DERIVATIVES FROM N-DIENYL-GAMMA-LACTAMS/

Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regiose lectivity to the oxazine adducts 5a,b (Scheme 1). Sequential osmylatio n, protection of the ensuing glycol, and reduction of the N-O bond gav e the expected hemiaminals 11a, b which were characterized by their cr ystalline sulfite adducts 12a,b (Schemes 1 and 2). Deprotection and sa ponification of the latter led to aminodeoxyerythrose and to aminodeox yribose derivatives as an equilibrium of pyrrolidinose equivalents, i. e., hemiaminals 14a,b, imines 14'a,b, and dimers 14''a,b, respectively (Scheme 3). Hydrocyanic acid addition to 11a,b led ultimately to the proline derivatives 16a,b (Scheme 2). Compound 11b proved to be an inh ibitor of syncytium formation in AIDS-infected calls.