Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules

被引:98
作者
Fraunhoffer, KJ [1 ]
Bachovchin, DA [1 ]
White, MC [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ol047800p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A hydrocarbon oxidation approach has been applied to the construction of several linear (E)-allylic alcohols that have served as intermediates in the synthesis of natural products and natural product-like molecules. In the original syntheses.. these intermediates were constructed using a standard Wittig-type olefination approach. We report here that routes to these same intermediates designed around a hydrocarbon oxidation approach are more efficient both in the total number of functional group manipulations (FGMs) and overall steps, as well as in the overall yield.
引用
收藏
页码:223 / 226
页数:4
相关论文
共 26 条
[1]   Copper catalyzed allylic oxidation with peresters [J].
Andrus, MB ;
Lashley, JC .
TETRAHEDRON, 2002, 58 (05) :845-866
[2]   SYNTHESIS OF 8,9-LEUKOTRIENE-C3 AND 8,9-LEUKOTRIENE-D3 [J].
BAKER, SR ;
BOOT, JR ;
MORGAN, SE ;
OSBORNE, DJ ;
ROSS, WJ ;
SHRUBSALL, PR .
TETRAHEDRON LETTERS, 1983, 24 (41) :4469-4472
[3]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[4]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[5]   A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].
Chen, MS ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347
[6]   KINETICALLY CONTROLLED TOTAL SYNTHESES OF DL-TRACHELANTHAMIDINE AND DL-ISORETRONECANOL [J].
DANISHEFSKY, S ;
MCKEE, R ;
SINGH, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (14) :4783-4788
[7]   USE OF SULFOXIDES AS COCATALYSTS IN THE PALLADIUM QUINONE-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES - AN EXAMPLE OF LIGAND-ACCELERATED CATALYSIS [J].
GRENNBERG, H ;
GOGOLL, A ;
BACKVALL, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5808-5811
[8]   PREPARATION OF ALLYLIC ACETATES FROM SIMPLE ALKENES BY PALLADIUM(II)-CATALYZED ACETOXYLATION [J].
HANSSON, S ;
HEUMANN, A ;
REIN, T ;
AKERMARK, B .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :975-984
[9]   4,5-diisopropyl-B-[(E)-[(3'-menthofuryl)dimethylsilyl]allyl]-1,3,2-dioxaborolane, an improved chiral reagent for the anti alpha-hydroxyallylation of aldehydes: Application to the enantioselective synthesis of (-)-swainsonine [J].
Hunt, JA ;
Roush, WR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1112-1124
[10]  
ICHIKAWA Y, 1993, SYNLETT, P907