Studies directed toward the total synthesis of scytophycin C: Synthesis of the C(1)-C(18) fragment of scytophycin C

被引:21
作者
Grieco, PA [1 ]
Speake, JD
机构
[1] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA
[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
D O I
10.1016/S0040-4039(97)10852-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the C(1) to C(18) fragment of Scytophycin C is described which features a highly stereoselective carbon Ferrier-type reaction in 3.0 M lithium perchlorate/ethyl acetate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1275 / 1278
页数:4
相关论文
共 16 条
[1]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[2]   STEREOSELECTIVE SYNTHESIS OF ALPHA-SINENSAL [J].
BUCHI, G ;
WUEST, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7573-7574
[3]  
COOK AF, 1966, CHEM IND-LONDON, P1141
[4]   MILD ALCOHOL METHYLATION PROCEDURES FOR THE SYNTHESIS OF POLYOXYGENATED NATURAL-PRODUCTS - APPLICATIONS TO THE SYNTHESIS OF LONOMYCIN-A [J].
EVANS, DA ;
RATZ, AM ;
HUFF, BE ;
SHEPPARD, GS .
TETRAHEDRON LETTERS, 1994, 35 (39) :7171-7172
[5]  
Grieco P. A., 1991, ALDRICHIM ACTA, V24, P59
[6]   SCYTOPHYCINS, CYTOTOXIC AND ANTIMYCOTIC AGENTS FROM THE CYANOPHYTE SCYTONEMA-PSEUDOHOFMANNI [J].
ISHIBASHI, M ;
MOORE, RE ;
PATTERSON, GML ;
XU, CF ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5300-5306
[7]   TOXINS FROM CYANOPHYTES BELONGING TO THE SCYTONEMATACEAE [J].
MOORE, RE ;
PATTERSON, GML ;
MYNDERSE, JS ;
BARCHI, J ;
NORTON, TR ;
FURUSAWA, E ;
FURUSAWA, S .
PURE AND APPLIED CHEMISTRY, 1986, 58 (02) :263-271
[8]   Total synthesis of swinholide A [J].
Nicolaou, KC ;
Ajito, K ;
Patron, AP ;
Khatuya, H ;
Richter, PK ;
Bertinato, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3059-3060
[9]   TOTAL SYNTHESIS OF SWINHOLIDE-A AND HEMISWINHOLIDE-A [J].
PATERSON, I ;
YEUNG, KS ;
WARD, RA ;
CUMMING, JG ;
SMITH, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9391-9392
[10]   THE TOTAL SYNTHESIS OF SWINHOLIDE-A .4. SYNTHESIS OF SWINHOLIDE-A AND ISOSWINHOLIDE-A FROM THE PROTECTED MONOMERIC SECO ACID, PRE-SWINHOLIDE-A [J].
PATERSON, I ;
YEUNG, KS ;
WARD, RA ;
SMITH, JD ;
CUMMING, JG ;
LAMBOLEY, S .
TETRAHEDRON, 1995, 51 (34) :9467-9486