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(±)‐4‐Amino‐4,5‐dideoxyribose, (±)‐4‐amino‐4‐deoxyerythrose, and (±)‐dihydroxyproline derivatives from N ‐dienyl‐γ‐lactams
Author(s) -
Behr JeanBernard,
Defoin Albert,
Mahmood Naheed,
Streith Jacques
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780510
Subject(s) - chemistry , saponification , adduct , regioselectivity , cycloaddition , stereochemistry , ring (chemistry) , amino acid , medicinal chemistry , organic chemistry , catalysis , biochemistry
Hetero‐ Diels ‐ Alder cycloaddition of acylnitroso dienophile 4 with the N ‐(butadienyl)pyrrolidinone derivatives 2a , b led with complete regioselectivity to the oxazine adducts 5a , b ( Scheme 1 ). Sequential osmylation, protection of the ensuing glycol, and reduction of the NO bond gave the expected hemiaminals 11a , b which were characterized by their crystalline sulfite adducts 12a , b ( Schemes 1 and 2 ). Deprotection and saponification of the latter led to aminodeoxyerythrose and to aminodeoxyribose 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 inhibitor of syncytium formation in AIDS‐infected cells.