First comprehensive bakkane approach:: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide A, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C

被引:72
作者
Brocksom, TJ [1 ]
Coelho, F [1 ]
Deprés, JP [1 ]
Greene, AE [1 ]
de Lima, MEF [1 ]
Hamelin, O [1 ]
Hartmann, B [1 ]
Kanazawa, AM [1 ]
Wang, YY [1 ]
机构
[1] Univ Grenoble 1, LEDSS, F-38041 Grenoble, France
关键词
D O I
10.1021/ja0208456
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro beta-methylene-gamma-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.
引用
收藏
页码:15313 / 15325
页数:13
相关论文
共 164 条
[91]   THE ACID-CATALYZED CYCLIZATION OF DIAZOKETONES - PREPARATION OF 2,4(3H,5H) FURANDIONES [J].
MILLER, RD ;
THEIS, W .
TETRAHEDRON LETTERS, 1987, 28 (10) :1039-1042
[92]   SYNTHETIC SCOPE OF TRIETHYLOXONIUM ION CATALYZED HOMOLOGATION OF KETONES WITH DIAZOACETIC ESTERS [J].
MOCK, WL ;
HARTMAN, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (03) :459-465
[93]   MECHANISM OF TRIETHYLOXONIUM ION CATALYZED HOMOLOGATION OF KETONES WITH DIAZOACETIC ESTERS [J].
MOCK, WL ;
HARTMAN, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (03) :466-472
[94]  
Molander G.A., 1995, ORGANIC REACTIONS, V46, P211, DOI DOI 10.1002/0471264180.OR046.03
[95]   Sequencing reactions with samarium(II) iodide [J].
Molander, GA ;
Harris, CR .
CHEMICAL REVIEWS, 1996, 96 (01) :307-338
[96]   APPLICATION OF LANTHANIDE REAGENTS IN ORGANIC-SYNTHESIS [J].
MOLANDER, GA .
CHEMICAL REVIEWS, 1992, 92 (01) :29-68
[97]  
MORI K, 1995, SYNTHESIS-STUTTGART, P845, DOI 10.1055/s-1995-4004
[98]   A simple and efficient preparation of propargylic β-keto esters through transesterification [J].
Mottet, C ;
Hamelin, O ;
Garavel, G ;
Deprés, JP ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1380-1382
[99]  
MULLER P, 1973, TETRAHEDRON LETT, P3565
[100]   PREPARATION OF NATURALLY-OCCURRING ALPHA-TERTHIOPHENES (2,2'-5',2''-TERTHIOPHENES) [J].
NAKAYAMA, J ;
NAKAMURA, Y ;
TAJIRI, T ;
HOSHINO, M .
HETEROCYCLES, 1986, 24 (03) :637-640