Facile synthesis of saturated eight-membered ring lactones

被引:23
作者
Buszek, KR [1 ]
Jeong, Y [1 ]
Sato, N [1 ]
Still, PC [1 ]
Muiño, PL [1 ]
Ghosh, I [1 ]
机构
[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
关键词
D O I
10.1081/SCC-100104408
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of functionalized saturated eight-membered ring lactones from their corresponding seco acids is a very facile process using conventional macrolactonization protocols. This heretofore unrecognized and overlooked strategy is illustrated for several examples. A possible explanation for the success of this approach is also presented.
引用
收藏
页码:1781 / 1791
页数:11
相关论文
共 22 条
[1]  
ACKLAND JJ, 1985, J CHEM SOC P1, P843
[2]   THE CONFORMATIONAL EFFECTS OF QUATERNARY CENTERS [J].
ALDER, RW ;
MAUNDER, CM ;
ORPEN, AG .
TETRAHEDRON LETTERS, 1990, 31 (46) :6717-6720
[3]  
ALLINGER NL, 1982, PURE APPL CHEM, V54, P2512
[4]   The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].
Beesley, RM ;
Ingold, CK ;
Thorpe, JF .
JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106
[5]   PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].
BODEN, EP ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395
[6]   AN IMPROVED SYNTHESIS OF THE OCTALACTINS [J].
BUSZEK, KR ;
JEONG, Y .
TETRAHEDRON LETTERS, 1995, 36 (40) :7189-7192
[7]   TOTAL SYNTHESIS OF OCTALACTIN-A AND OCTALACTIN-B [J].
BUSZEK, KR ;
SATO, N ;
JEONG, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5511-5512
[8]   EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].
COREY, EJ ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616
[9]   A 2ND GENERATION FORCE-FIELD FOR THE SIMULATION OF PROTEINS, NUCLEIC-ACIDS, AND ORGANIC-MOLECULES [J].
CORNELL, WD ;
CIEPLAK, P ;
BAYLY, CI ;
GOULD, IR ;
MERZ, KM ;
FERGUSON, DM ;
SPELLMEYER, DC ;
FOX, T ;
CALDWELL, JW ;
KOLLMAN, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5179-5197
[10]   THE USE OF TERT-BUTYL ACETOTHIOACETATE AS A ROUTE TO BIS-BETA-KETOMACROLIDES [J].
FOX, CMJ ;
LEY, SV ;
SLAWIN, AMZ ;
WILLIAMS, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (24) :1805-1806