Both anti and syn enantiomerically pure functionalized α -amino-β-hydroxy acids and derivatives were synthesized starting from norephedrine-derived oxazolidine (1). The key-steps of the synthesis were the nucleophilic epoxidation of (1) and the nucleophilic opening of epoxy acid (3) with ammonia, both reactions proved regio- and diastereospecific. High yield preparation of the target anti aldehyde (9) was accomplished using standard procedures. The complementary syn aldehyde (23) was obtained via alkaline isomerization of the cis oxazolidinone (13) to the trans one. The aldehyde function of (9) and (23) provides a useful handle for manipulation to more complex structures, allowing potential access to a range of optically pure α -amino-β-hydroxy acids. The formal total synthesis of the monocyclic β-lactam antibiotic "carumonam" was accomplished using the present methodology.

ASYMMETRIC-SYNTHESIS OF FUNCTIONALIZED ALPHA-AMINO-BETA-HYDROXY ACIDS VIA CHIRAL NOREPHEDRINE-DERIVED OXAZOLIDINES / S. CARDANI, A. BERNARDI, L. COLOMBO, C.M.A. GENNARI, C. SCOLASTICO, I. VENTURINI. - In: TETRAHEDRON. - ISSN 0040-4020. - 44:17(1988), pp. 5563-5572.

ASYMMETRIC-SYNTHESIS OF FUNCTIONALIZED ALPHA-AMINO-BETA-HYDROXY ACIDS VIA CHIRAL NOREPHEDRINE-DERIVED OXAZOLIDINES

A. BERNARDI;C.M.A. GENNARI;C. SCOLASTICO;
1988

Abstract

Both anti and syn enantiomerically pure functionalized α -amino-β-hydroxy acids and derivatives were synthesized starting from norephedrine-derived oxazolidine (1). The key-steps of the synthesis were the nucleophilic epoxidation of (1) and the nucleophilic opening of epoxy acid (3) with ammonia, both reactions proved regio- and diastereospecific. High yield preparation of the target anti aldehyde (9) was accomplished using standard procedures. The complementary syn aldehyde (23) was obtained via alkaline isomerization of the cis oxazolidinone (13) to the trans one. The aldehyde function of (9) and (23) provides a useful handle for manipulation to more complex structures, allowing potential access to a range of optically pure α -amino-β-hydroxy acids. The formal total synthesis of the monocyclic β-lactam antibiotic "carumonam" was accomplished using the present methodology.
Settore CHIM/06 - Chimica Organica
TETRAHEDRON
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/176995
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