Total Synthesis of Polygalolide A

被引:8
作者
Adachi, Masaatsu [1 ]
Yamada, Hitomi [1 ]
Isobe, Minoru [2 ]
Nishikawat, Toshio [1 ]
机构
[1] Nagoya Univ, Grad Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan
[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
基金
日本学术振兴会;
关键词
INTRAMOLECULAR-C-ARYLATION; SECONDARY ALCOHOLS; GLYCOSIDATION; CYCLOADDITION; ALKYNYL; TRIBUTYLPHOSPHINE; DEOXYGENATION; EPIMERIZATION; COMPLEXES; PRODUCTS;
D O I
10.1021/ol2028256
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of polygalolide A was accomplished through intramolecular C-glycosylation of glucal modified with siloxyfuran. The siloxyfuran group and siloxy substituent at the C-3 position played crucial roles in allowing direct access to the highly substituted oxabicyclo[3.2.1] core skeleton with correct quaternary stereogenic centers.
引用
收藏
页码:6532 / 6535
页数:4
相关论文
共 32 条
[1]   A SIMPLE AND READY INTERNAL C-GLYCOSYLATION OF 2,3,5-TRI-O-BENZYLGLYCOFURANOSES PROMOTED BY THE BORON-TRIFLUORIDE DIETHYL-ETHER COMPLEX [J].
ANASTASIA, M ;
ALLEVI, P ;
CIUFFREDA, P ;
FIECCHI, A ;
SCALA, A .
CARBOHYDRATE RESEARCH, 1990, 208 :264-266
[2]   STRUCTURAL ELUCIDATION AND A NOVEL REDUCTIVE CLEAVAGE OF RIBOFURANOSYL RING C-1-O-BOND OF THE INTRAMOLECULAR C-ARYLATION PRODUCT OF TRI-O-BENZYL-BETA-D-RIBOFURANOSYL FLUORIDE [J].
ARAKI, Y ;
MOKUBO, E ;
KOBAYASHI, N ;
NAGASAWA, J ;
ISHIDO, Y .
TETRAHEDRON LETTERS, 1989, 30 (09) :1115-1118
[3]   ON THE MECHANISM OF THE DEOXYGENATION OF SECONDARY ALCOHOLS BY THE REDUCTION OF THEIR METHYL XANTHATES BY TIN HYDRIDES [J].
BARTON, DHR ;
CRICH, D ;
LOBBERDING, A ;
ZARD, SZ .
TETRAHEDRON, 1986, 42 (08) :2329-2338
[4]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[5]   The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings [J].
Battiste, MA ;
Pelphrey, PM ;
Wrightthl, DL .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3438-3447
[6]   DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].
BOLITT, V ;
MIOSKOWSKI, C ;
LEE, SG ;
FALCK, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813
[7]   Efficient synthesis of (E)-3-alkylidene-2(3H)-furanones from 3-(1-hydroxyalkyl)-2-silyloxyfurans [J].
Boukouvalas, John ;
Marion, Olivier .
SYNLETT, 2006, (10) :1511-1514
[8]   STEREOSELECTIVE TEMPLATE-DIRECTED C-GLYCOSIDATION - SILVER(I)-MEDIATED INTRAMOLECULAR REACTIONS OF (2-PYRIDYLTHIO)GLYCOSIDIC SILYL ENOL ETHERS [J].
CRAIG, D ;
MUNASINGHE, VRN .
TETRAHEDRON LETTERS, 1992, 33 (05) :663-666
[9]   Total Synthesis of Ciguatoxin [J].
Hamajima, Akinari ;
Isobe, Minoru .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2941-2945
[10]   Asymmetric catalytic [4+3] cycloaddition reactions [J].
Harmata, Michael .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2297-2306