A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step

被引:30
作者
Griffiths-Jones , Charlotte M. [1 ]
Knight, David W. [1 ]
机构
[1] Cardiff Univ, Sch Chem, Main Coll, Cardiff CF10 3AT, S Glam, Wales
基金
英国工程与自然科学研究理事会;
关键词
alpha-Cyclopiazonic acid; Synthesis; Carbenium ion; Cascade; Indole alkaloid; ALPHA-CYCLOPIAZONIC ACID; PENICILLIUM-CYCLOPIUM; STEREOSELECTIVE-SYNTHESIS; N-BOC; BIOSYNTHESIS; ROUTE; OXIDOCYCLASE; NITROACETATE; DERIVATIVES; MYCOTOXINS;
D O I
10.1016/j.tet.2011.08.094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The indole alkaloid alpha-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8515 / 8528
页数:14
相关论文
共 53 条
[1]   Studies towards the synthesis of diazonamide A. Synthesis of the 4-(oxazol-5-ylmethyl) aryltryptamine fragment [J].
Bagley, MC ;
Moody, CJ ;
Pepper, AG .
TETRAHEDRON LETTERS, 2000, 41 (35) :6901-6904
[2]   REGIOSPECIFIC ADDITION OF ORGANOCOPPER REAGENTS TO ALPHA, BETA-UNSATURATED ESTERS [J].
BEHFOROUZ, M ;
CURRAN, TT ;
BOLAN, JL .
TETRAHEDRON LETTERS, 1986, 27 (27) :3107-3110
[3]   The Knight route to cyclopiazonic acid: enantioselective synthesis of a key intermediate [J].
Beyer, Christian ;
Scherkenbeck, Juergen ;
Sondermann, Frank ;
Figge, Axel .
TETRAHEDRON, 2010, 66 (35) :7119-7123
[4]   ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN [J].
BUSH, EJ ;
JONES, DW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) :1200-1201
[5]   SYNTHESIS OF N-ALKYL DERIVATIVES OF 4-(2'-AMINOETHYL)INDOLE [J].
CANNON, JG ;
DEMOPOULOS, BJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) :1195-1199
[6]   BIOSYNTHESIS OF ALPHA-CYCLOPIAZONIC ACID - STEREOCHEMICAL ASPECTS OF D-RING FORMATION [J].
CHALMERS, AA ;
GORSTALLMAN, CP ;
STEYN, PS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (24) :1367-1368
[7]   CHEMISTRY OF OXAZIRIDINES .9. SYNTHESIS OF 2-SULFONYLOXAZIRIDINES AND 2-SULFAMYLOXAZIRIDINES USING POTASSIUM PEROXYMONOSULFATE (OXONE) [J].
DAVIS, FA ;
CHATTOPADHYAY, S ;
TOWSON, JC ;
LAL, S ;
REDDY, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2087-2089
[8]   PRODUCTION OF MYCOTOXINS BY PENICILLIUM SPECIES [J].
ELBANNA, AA ;
PITT, JI ;
LEISTNER, L .
SYSTEMATIC AND APPLIED MICROBIOLOGY, 1987, 10 (01) :42-46
[9]   A NOVEL SYNTHESIS OF THE NATURALLY-OCCURRING DIBENZOFURANS PANNARIC ACID AND SCHIZOPELTIC ACID [J].
ELIX, JA ;
PARKER, JL .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (01) :187-192
[10]   Triproline analogues of Pro-Leu-Gly-NH2 with Pro/Leu and Pro/Phe chimeric amino acids in position 2 [J].
Evans, MC ;
Johnson, RL .
TETRAHEDRON, 2000, 56 (50) :9801-9808