A novel synthesis of (±) 2-epi-validamine

被引:6
作者
Afarinkia, K [1 ]
Mahmood, F [1 ]
机构
[1] Univ London Kings Coll, Dept Chem, London WC2R 2LS, England
关键词
D O I
10.1016/S0040-4039(98)01610-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-) 2-epi-Validamine is synthesised in five steps by the chemical manipulation of bicyclic lactone cycloadduct of ethyl coumalate and vinylene carbonate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7413 / 7414
页数:2
相关论文
共 9 条
[1]   A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS [J].
ACENA, JL ;
ARJONA, O ;
DELAPRADILLA, RF ;
PLUMET, J ;
VISO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6419-6424
[2]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[3]   STUDIES ON VALIDAMYCINS, NEW ANTIBIOTICS .6. VALIDAMINE, HYDROXYVALIDAMINE AND VALIDATOL, NEW CYCLITOLS [J].
HORII, S ;
IWASA, T ;
MIZUTA, E ;
KAMEDA, Y .
JOURNAL OF ANTIBIOTICS, 1971, 24 (01) :59-&
[4]  
Iwasa T., 1970, J. Antibiot, V23, P595, DOI [10.7164/antibiotics.23.595, DOI 10.7164/ANTIBIOTICS.23.595]
[5]   TANDEM PERICYCLIC-REACTIONS (TPR) - A SIMPLE CONSTRUCTION OF FUNCTIONALIZED [3,N,1] BICYCLES AND A READY ENTRY INTO THE CORE OF GIBBERELLIC-ACID AND ZIZAENE [J].
MARKO, IE ;
SERES, P ;
EVANS, GR ;
SWARBRICK, TM .
TETRAHEDRON LETTERS, 1993, 34 (45) :7305-7308
[6]   PSEUDO-SUGARS .6. SYNTHESIS OF 6 ISOMERS OF 5-HYDROXYMETHYL-1,2,3,4-CYCLOHEXANETETROL (PSEUDO-HEXOPYRANOSE) AND THEIR DERIVATIVES [J].
OGAWA, S ;
ARA, M ;
KONDOH, T ;
SAITOH, M ;
MASUDA, R ;
TOYOKUNI, T ;
SUAMI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1121-1126
[7]   NEW METHOD FOR DIRECT CONVERSION OF AMIDES TO AMINES [J].
RADHAKRISHNA, AS ;
PARHAM, ME ;
RIGGS, RM ;
LOUDON, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1746-1747
[8]   ENANTIOSPECIFIC SYNTHESES OF PENTA-N,O,O,O,O-ACETYLVALIDAMINE AND PENTA-N,O,O,O,O-ACETYL-2-EPI-VALIDAMINE [J].
SHING, TKM ;
TAI, VWF .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5332-5334
[9]   A NEW SYNTHETIC APPROACH TO PSEUDO-SUGARS BY ASYMMETRIC DIELS-ALDER REACTION - SYNTHESIS OF OPTICALLY PURE PSEUDO-BETA-D-MANNOPYRANOSE, 1-AMINO-1-DEOXYPSEUDO-ALPHA-D-MANNOPYRANOSE AND PSEUDO-ALPHA-L-MANNOPYRANOSE DERIVATIVES [J].
TAKAHASHI, T ;
KOTSUBO, H ;
IYOBE, A ;
NAMIKI, T ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3065-3072