Formal total synthesis of (±)-α- and β-cedrene by preparation of cedrone.: Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation

被引:52
作者
Kerr, WJ [1 ]
McLaughlin, M [1 ]
Morrison, AJ [1 ]
Pauson, PL [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
关键词
D O I
10.1021/ol016054a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The cedrene carbon skeleton was rapidly assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Khand cyclization reaction. Further synthetic manipulations provided a concise formal total synthesis of alpha- and beta -cedrene.
引用
收藏
页码:2945 / 2948
页数:4
相关论文
共 39 条
[1]   Sesquiterpenes from Juniperus thurifera L. stereochemistry in unusual cedrane and duprezianane series [J].
Barrero, AF ;
del Moral, JQ ;
Lara, A .
TETRAHEDRON, 2000, 56 (23) :3717-3723
[2]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[3]   TOTAL SYNTHESIS OF (+/-)-CEDROL AND (+/-)-CEDRENE VIA AN INTRA-MOLECULAR DIELS-ALDER REACTION [J].
BREITHOLLE, EG ;
FALLIS, AG .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1964-1968
[4]  
Brown DS, 2000, SYNLETT, P1573
[5]  
CALDWELL JJ, UNPUB
[6]   Preparation and reaction of desymmetrised cobalt alkyne complexes [J].
Carbery, DR ;
Kerr, WJ ;
Lindsay, DM ;
Scott, JS ;
Watson, SP .
TETRAHEDRON LETTERS, 2000, 41 (17) :3235-3239
[7]   PROMOTERS FOR THE (ALKYNE)HEXACARBONYLDICOBALT-BASED CYCLOPENTENONE SYNTHESIS [J].
CHUNG, YK ;
LEE, BY ;
JEONG, N ;
HUDECEK, M ;
PAUSON, PL .
ORGANOMETALLICS, 1993, 12 (01) :220-223
[8]   Synthesis of analogues of methyl jasmonate using the formation of cyclopentenones from alkyne(hexacarbonyl)dicobalt complexes [J].
Clements, CJ ;
Dumoulin, D ;
Hamilton, DR ;
Hudecek, M ;
Kerr, WJ ;
Kiefer, M ;
Moran, PH ;
Pauson, PL .
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (10) :636-637
[9]  
CLEMENTS CJ, 1988, J CHEM RES MINIPRINT, P2658
[10]   TOTAL SYNTHESIS OF DL-CEDRENE AND DL-CEDROL [J].
COREY, EJ ;
GIROTRA, NN ;
MATHEW, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1557-&