A Four-Step Total Synthesis of Radermachol

被引:32
作者
Buccini, Marco [1 ]
Piggott, Matthew J. [1 ]
机构
[1] Univ Western Australia, Sch Chem & Biochem, Perth, WA 6009, Australia
关键词
ENOL ETHERS; PRODUCT; SYSTEM;
D O I
10.1021/ol500862w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radermachol has been synthesized in four steps and an overall yield of 22% via key ytterbium triflate catalyzed furannulation and intramolecular nucleophilic acylation reactions.
引用
收藏
页码:2490 / 2493
页数:4
相关论文
共 36 条
[1]   A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial [J].
Alvey, Luke ;
Prado, Soizic ;
Huteau, Valerie ;
Saint-Joanis, Brigitte ;
Michel, Sylvie ;
Koch, Michel ;
Cole, Stewart T. ;
Tillequin, Francois ;
Janin, Yves L. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) :8264-8272
[2]   SYNTHESIS OF THE GRISEUSIN-A RING-SYSTEM [J].
BRIMBLE, MA ;
NAIRN, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :169-171
[3]   SYNTHESIS OF THE CIS-3A,8B-DIHYDROFURO[3,2-B]BENZOFURAN-2(3H)-ONE RING-SYSTEM VIA A FUROFURAN ANNULATION TO ACTIVATED BENZOQUINONES [J].
BRIMBLE, MA ;
BRIMBLE, MT ;
GIBSON, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :179-184
[4]   APPROACHES TO A KEY LACTONE INTERMEDIATE REQUIRED FOR THE SYNTHESIS OF PYRANONAPHTHOQUINONE ANTIBIOTICS [J].
BRIMBLE, MA ;
SPICER, JA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (02) :197-205
[5]  
Brirnble M. A., 1998, TETRAHEDRON LETT, V39, P5647
[6]   Bisannulation of 2,3-Dichloro-1,4-naphthoquinone with o-Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine [J].
Buccini, Marco ;
Jeow, Shi Yuan ;
Byrne, Lindsay ;
Skelton, Brian W. ;
Tuan Minh Nguyen ;
Chai, Christina L. L. ;
Piggott, Matthew J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (16) :3232-3240
[7]   SYNTHESIS OF SOME ARYLATED QUINONES [J].
CAMERON, DW ;
FEUTRILL, GI ;
PATTI, AF ;
PERLMUTTER, P ;
SEFTON, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (07) :1501-1508
[8]   NUCLEOPHILIC ALKENES .5. FORMATION OF A NAPHTHALENIC SYSTEM BY ADDITION OF 1,1-DIMETHOXYETHENE TO 2-ACETYL-1,4-BENZOQUINONE AND SUBSEQUENT TRANSFORMATION [J].
CAMERON, DW ;
FEUTRILL, GI ;
SEFTON, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (09) :2099-2101
[9]   A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .2. FROM ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES [J].
CAZEAU, P ;
DUBOUDIN, F ;
MOULINES, F ;
BABOT, O ;
DUNOGUES, J .
TETRAHEDRON, 1987, 43 (09) :2089-2100
[10]  
CRABTREE SR, 1990, SYNLETT, P169