Progress towards the total synthesis of trichodermamides A and B:: Construction of the oxazine ring moiety

被引:25
作者
Wan, Xiaobo [1 ]
Doridot, Gabriel [1 ]
Joullie, Madeleine M. [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol062993x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trichodermamides are modified heterocyclic dipeptides that possess a unique 4H-5,6-dihydro-1,2-oxazine ring. Starting from affordable, easily available (-)-quinic acid, the enantioselective synthesis of this oxazine moiety was achieved by an intramolecular epoxide ring-opening reaction by an oxime.
引用
收藏
页码:977 / 980
页数:4
相关论文
共 21 条
[11]   Novel and versatile synthesis of pyrrolidine type azasugars, DAB-1 and LAB-1, potent glucosidase inhibitors [J].
Kim, YJ ;
Kido, M ;
Bando, M ;
Kitahara, T .
TETRAHEDRON, 1997, 53 (22) :7501-7508
[12]   Manganese-catalyzed epoxidations of alkenes in bicarbonate solutions [J].
Lane, BS ;
Vogt, M ;
DeRose, VJ ;
Burgess, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11946-11954
[13]   Penicillazine, a unique quinolone derivative with 4H-5,6-dihydro-1,2-oxazine ring system from the marine fungus Penicillium sp (strain #386) from the South China Sea [J].
Lin, YC ;
Shao, ZY ;
Jiang, GC ;
Zhou, SN ;
Cai, JW ;
Vrijmoed, LLP ;
Jones, EBG .
TETRAHEDRON, 2000, 56 (49) :9607-9609
[14]   SYN-STEREOSELECTIVE EPOXIDATION OF ALLYLIC ETHERS USING CF3CO3H [J].
MCKITTRICK, BA ;
GANEM, B .
TETRAHEDRON LETTERS, 1985, 26 (40) :4895-4898
[15]   Total synthesis of abyssomicin C and atrop-abyssomicin C [J].
Nicolaou, K. C. ;
Harrison, Scott T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (20) :3256-3260
[16]   SYNTHESIS OF MACROCYCLES BY INTRA-MOLECULAR KETOPHOSPHONATE REACTIONS - STEREOSELECTIVE CONSTRUCTION OF THE LEFT-WING OF CARBOMYCIN-B AND A SYNTHESIS OF DL-MUSCONE FROM OLEIC-ACID [J].
NICOLAOU, KC ;
SEITZ, SP ;
PAVIA, MR ;
PETASIS, NA .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :4011-4013
[17]   EPOXIDATIONS WITH 30-PERCENT HYDROGEN-PEROXIDE CATALYZED BY TUNGSTIC ACID IN BUFFERED MEDIA [J].
PRAT, D ;
LETT, R .
TETRAHEDRON LETTERS, 1986, 27 (06) :707-710
[18]   HIGH STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN TRANSITION-METAL CATALYZED EPOXIDATIONS OF OLEFINIC ALCOHOLS BY TERT-BUTYL HYDROPEROXIDE [J].
SHARPLES.KB ;
MICHAELS.RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6136-6137
[19]   SYNTHESIS OF OPTICALLY-ACTIVE 4-HYDROXYALKANENITRILES VIA AN ENZYMATIC-REACTION [J].
TAKAGI, Y ;
ITOH, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (10) :2949-2953
[20]   TOTAL SYNTHESIS AND STRUCTURE ASSIGNMENT OF THE ANTITUMOR ANTIBIOTIC ARANOROSIN [J].
WIPF, P ;
KIM, Y ;
FRITCH, PC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7195-7203