TY  - JOUR
AU  - Gyónfalvi, Szilvia
AU  - Szakonyi, Zsolt
AU  - Fülöp, Ferenc
TI  - Synthesis and transformation of novel cyclic beta-amino acid derivatives from (+)-3-carene
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 14
PY  - 2003
IS  - 24
SP  - 3965
EP  - 3972
PG  - 8
SN  - 0957-4166
DO  - 10.1016/j.tetasy.2003.10.001
UR  - https://m2.mtmt.hu/api/publication/1013516
ID  - 1013516
AB  - The regio- and stereoselective addition of chlorosulfonyl isocyanate to (+)-3-carene 1 resulted in beta-lactam 2, which was converted to N-Boc-beta-amino acid 4, beta-amino ester 7, and carboxamide derivatives 18 and 20 via N-Boc activation and mild ring opening. The corresponding beta-amino ester 7 was transformed to 2-thioxopyrimidin-4-one 11 and 2,4-pyrimidinedione 13. LAH reduction of 5 and 7 resulted in amino alcohols 6 and 8. The reaction of 8 with phenyl isothiocyanate, followed by cyclisation, furnished 1,3-oxazine 15. (C) 2003 Elsevier Ltd. All rights reserved.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Szakonyi, Zsolt
AU  - Martinek, Tamás
AU  - Hetényi, Anasztázia
AU  - Fülöp, Ferenc
TI  - Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 11
PY  - 2000
IS  - 22
SP  - 4571
EP  - 4579
PG  - 9
SN  - 0957-4166
DO  - 10.1016/S0957-4166(00)00435-3
UR  - https://m2.mtmt.hu/api/publication/1014481
ID  - 1014481
N1  - Cited By :50            
            Export Date: 8 September 2023            
            CODEN: TASYE            
            Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu
AB  - Regio- and stereospecific addition of chlorosulfonyl isocyanate 
to (+)- and (-)-alpha -pinene I resulted in enantiomerically 
pure beta -lactams 2, which were converted to enantiomeric beta 
-amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The 
resulting 1,3-difunctional compounds 3, 4 and 6 were transformed 
to fused saturated 1,3-heterocycles such as tetrahydro-1,3-
oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-
4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights 
reserved.
LA  - English
DB  - MTMT
ER  -