HYDROXYLAMINE-ALKYNE CYCLIZATIONS - SYNTHESIS OF THE 7-MEMBERED LACTAM STRUCTURE PROPOSED FOR (+/-)-ACACIALACTAM

被引:10
作者
FOX, ME
HOLMES, AB
FORBES, IT
THOMPSON, M
ZILLER, JW
机构
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AD,ENGLAND
[3] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
关键词
D O I
10.1016/S0040-4039(00)60206-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclic nitrone 2 was converted via the key intermediates 7, 12 and 14 into the seven-membered lactam structure 3 proposed for acacialactam. The spectra of the synthetic material differed from that of the natural product for which an alternative structure is tentatively proposed.
引用
收藏
页码:7425 / 7428
页数:4
相关论文
共 16 条
[1]   SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS [J].
BHATTACHARYA, A ;
DIMICHELE, LM ;
DOLLING, UH ;
DOUGLAS, AW ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3318-3319
[2]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[3]   TOTAL SYNTHESIS OF PICROTOXININ [J].
COREY, EJ ;
PEARCE, HL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) :5841-5843
[4]   GENERATION AND SYNTHETIC USE OF METALLATED DIMETHYLHYDRAZONES REGION AND STEREOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS [J].
COREY, EJ ;
ENDERS, D .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04) :1337-1361
[5]   HYDROXYLAMINE-ALKYNE CYCLIZATIONS - SYNTHESIS OF THE 7-MEMBERED LACTAM STRUCTURE PROPOSED FOR (+/-)-ACACIALACTAM [J].
FOX, ME ;
HOLMES, AB ;
FORBES, IT ;
THOMPSON, M ;
ZILLER, JW .
TETRAHEDRON LETTERS, 1992, 33 (48) :7425-7428
[6]   SYNTHESIS OF THE BOTTOM HALF OF CHLOROTHRICOLIDE [J].
HALL, SE ;
ROUSH, WR .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4611-4621
[7]   ORGANOALUMINUM-PROMOTED BECKMANN REARRANGEMENT OF OXIME SULFONATES [J].
MARUOKA, K ;
MIYAZAKI, T ;
ANDO, M ;
MATSUMURA, Y ;
SAKANE, S ;
HATTORI, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2831-2843
[8]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467
[10]   ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS 167B AND 209D [J].
POLNIASZEK, RP ;
BELMONT, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4688-4693