Facile synthesis of 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols

被引:37
作者
Chen, CL [1 ]
Martin, SF [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ol048517t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed ring opening of dimethoxy oxabenzonorbornadiene with aryl or vinyl halides occurred under very mild conditions to give substituted 1,2-dihydronaphthols that were oxidized with IBX to furnish substituted naphthols in excellent overall yields.
引用
收藏
页码:3581 / 3584
页数:4
相关论文
共 23 条
[1]   General entries to C-aryl glycosides.: Formal synthesis of galtamycinone [J].
Apsel, B ;
Bender, JA ;
Escobar, M ;
Kaelin, DE ;
Lopez, OD ;
Martin, SF .
TETRAHEDRON LETTERS, 2003, 44 (05) :1075-1077
[2]   Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents [J].
Arrayás, RG ;
Cabrera, S ;
Carretero, JC .
ORGANIC LETTERS, 2003, 5 (08) :1333-1336
[3]   Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol [J].
Bertozzi, F ;
Pineschi, M ;
Macchia, F ;
Arnold, LA ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2002, 4 (16) :2703-2705
[4]   Synthesis of the monomeric unit of gamma-actinorhodin [J].
Brimble, MA ;
Duncalf, LJ ;
Phythian, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1399-1403
[5]   ADDITION OF BUTYLLITHIUMS TO BENZONORBORNADIENE AND 1,4-DIHYDRONAPHTHALENE 1,4-ENDO-OXIDE [J].
CAPLE, R ;
CHEN, GMS ;
NELSON, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (19) :2874-&
[6]  
Chiu P, 1997, TOP CURR CHEM, V190, P1
[7]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963
[8]   PALLADIUM-CATALYZED REDUCTIVE COUPLINGS OF ORGANIC HALIDES WITH 7-HETEROATOM NORBORNADIENES - NEW SYNTHETIC METHODS FOR SUBSTITUTED ARYLS AND CIS-1,2-DIHYDRO-1-NAPHTHYL ALCOHOLS AND CARBAMATES [J].
DUAN, JP ;
CHENG, CH .
ORGANOMETALLICS, 1995, 14 (04) :1608-1618
[9]   Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides [J].
Feng, CC ;
Nandi, M ;
Sambaiah, T ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3538-3543
[10]  
Fugami K, 1998, SYNLETT, P477