Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones.: First total synthesis of both enantiomers of pipermethystine

被引：33
作者：
Arrayás, RG [1 ]
Alcudia, A [1 ]
Liebeskind, LS [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 21期
关键词：
D O I：
10.1021/ol010183+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(lh)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.
引用
收藏
页码：3381 / 3383
页数：3
相关论文
共 43 条
[1]   STEREOCONTROLLED SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-ALLITOL (1-DEOXY-ALLONOJIRIMYCIN) FROM SERINE [J].
ALTENBACH, HJ ;
HIMMELDIRK, K .
TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1077-1080
[2]  
[Anonymous], 1985, ALKALOIDS CHEM BIOL
[3]  
Arisawa M, 1997, SYNLETT, P1179
[4]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[5]   An efficient and facile three-step synthesis of 5-amino-5-deoxy-D-pentonolactams from unprotected D-pentono-1,4-lactones. [J].
Bouchez, V ;
Stasik, I ;
Beaupere, D ;
Uzan, R .
TETRAHEDRON LETTERS, 1997, 38 (44) :7733-7736
[6]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[7]   Ring closing metathesis of vinyl glycine derivatives [J].
Campagne, JM ;
Ghosez, L .
TETRAHEDRON LETTERS, 1998, 39 (34) :6175-6178
[8]   Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones [J].
Casamitjana, N ;
López, V ;
Jorge, A ;
Bosch, J ;
Molins, F ;
Roig, A .
TETRAHEDRON, 2000, 56 (24) :4027-4042
[9]   Thirty years of discovering arthropod alkaloids in amphibian skin [J].
Daly, JW .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (01) :162-172
[10]   Asymmetric synthesis of pentono- and 6-deoxyhexono-δ-lactams via hetero-Diels-Alder reactions with nitroso dienophile [J].
Defoin, A ;
Sarazin, H ;
Sifferlen, T ;
Strehler, C ;
Streith, J .
HELVETICA CHIMICA ACTA, 1998, 81 (08) :1417-1428
12345