A diastereoselective total synthesis of the sesquiterpene (±)-mutisianthol

被引:29
作者
Ferraz, HMC [1 ]
Aguilar, AM [1 ]
Silva, LF [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim, BR-05513970 Sao Paulo, Brazil
基金
巴西圣保罗研究基金会;
关键词
indan; total synthesis; ring contraction; thallium(III);
D O I
10.1016/S0040-4020(03)00974-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the phenolic sesquiterpene mutisianthol has been accomplished in 12 steps from the readily available 2-methylanisole. The required trans-1,3-disubstituted indan intermediate was obtained through a diastereoselective thallium(111) mediated ring contraction of a 1-methyl-1,2-dihydronaphthalene derivative. (C) 2003 Published by Elsevier Ltd.
引用
收藏
页码:5817 / 5821
页数:5
相关论文
共 24 条
[1]   Comparative study of anionic and radical Cyclization for the preparation of 1,3-dimethylindans:: Highly stereoselective preparation of cis-1,3-disubstituted Indans via intramolecular carbolithiation [J].
Bailey, WF ;
Mealy, MJ ;
Wiberg, KB .
ORGANIC LETTERS, 2002, 4 (05) :791-794
[2]   THE STEREOCHEMISTRY OF RING-CLOSURE OF SOME MONOSUBSTITUTED ORTHO-(BUT-3-ENYL)PHENYL RADICALS [J].
BECKWITH, ALJ ;
GERBA, S .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) :289-308
[3]   NATURAL TERPENE DERIVATIVES .88. COMPONENTS OF TRIBE MUTISIEAE [J].
BOHLMANN, F ;
ZDERO, C .
PHYTOCHEMISTRY, 1977, 16 (02) :239-242
[4]   NATURAL TERPENE DERIVATIVES .168. NEW GERANYLCOUMARIN DERIVATIVES AND OTHER COMPOUNDS FROM THE TRIBE MUTISIEAE [J].
BOHLMANN, F ;
ZDERO, C ;
LEVAN, N .
PHYTOCHEMISTRY, 1979, 18 (01) :99-102
[5]  
COPPOLA GM, 1984, SYNTHESIS-STUTTGART, P1021
[6]  
ELLISON RA, 1975, TETRAHEDRON LETT, P499
[7]   MARINE STEROLS .4. 24-DEHYDROCHOLESTEROL - ISOLATION FROM A BARNACLE AND SYNTHESIS BY THE WITTIG REACTION [J].
FAGERLUND, UHM ;
IDLER, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (24) :6473-6475
[8]  
Ferraz HMC, 2003, SYNTHESIS-STUTTGART, P1031
[9]   Construction of functionalized indans by thallium(III) promoted ring contraction of 3-alkenols [J].
Ferraz, HMC ;
Silva, LF .
TETRAHEDRON, 2001, 57 (50) :9939-9949
[10]   The reaction of 1-tetralones with thallium trinitrate supported on clay:: Ring contraction vs α-oxidation [J].
Ferraz, HMC ;
Silva, LF ;
Aguilar, AM ;
Vieira, TO .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (05) :680-684