Highly efficient synthesis of medium-sized lactones via oxidative lactonization: concise total synthesis of isolaurepan

被引:41
作者
Ebine, Makoto [1 ]
Suga, Yuto [1 ]
Fuwa, Haruhiko [1 ]
Sasaki, Makoto [1 ]
机构
[1] Tohoku Univ, Grad Sch Life Sci, Lab Biostruct Chem, Aoba Ku, Sendai, Miyagi 9818555, Japan
关键词
CYCLIC ETHERS; SELECTIVE OXIDATION; POLYCYCLIC ETHERS; MEDIUM-RING; ENANTIOSELECTIVE SYNTHESIS; CONVERGENT SYNTHESIS; HYDROGEN-TRANSFER; DIOLS; ALCOHOLS; PALLADIUM;
D O I
10.1039/b919673k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalytic amount of TEMPO in the presence of PhI(OAc)(2) effected oxidative lactonization of 1,6- and 1,7-diols, directly affording seven- and eight-membered lactones, respectively, in good yields.
引用
收藏
页码:39 / 42
页数:4
相关论文
共 58 条
[1]   N-oxidation of pyridine carboxylic acids using hydrogen peroxide catalyzed by a green heteropolyacid catalyst:: Preyssler's anion, [NaP5W30O110]14- [J].
Bamoharram, Fatemeh F. ;
Heravi, Majid M. ;
Roshani, Mina ;
Tavakoli, Niloofar .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 252 (1-2) :219-225
[2]  
BLOCH R, 1991, SYNLETT, P829
[3]  
Cameron A.F., 1965, J CHEM SOC, P638
[4]   A NEW SYNTHETIC METHOD FOR THE PREPARATION OF 2,8-DISUBSTITUTED OXOCANE DERIVATIVES - SYNTHESIS OF LAUTHISAN AND LAURENAN [J].
CARLING, RW ;
HOLMES, AB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :565-567
[5]   SYNTHESIS OF MEDIUM RING ETHERS .2. SYNTHESIS OF THE FULLY SATURATED CARBON SKELETON OF LAURENCIA NON-TERPENOID ETHER METABOLITES CONTAINING 7-MEMBERED, 8-MEMBERED AND 9-MEMBERED RINGS [J].
CARLING, RW ;
CLARK, JS ;
HOLMES, AB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :83-94
[6]   Enantioselective access to 2,7-cis-disubstituted oxepanes:: Formal synthesis of (+)-isolaurepan [J].
Carreño, MC ;
Mazery, RD ;
Urbano, A ;
Colobert, F ;
Solladié, G .
ORGANIC LETTERS, 2004, 6 (02) :297-299
[7]   Total synthesis of acanthacerebroside A and astrocerebroside A via a chiral epoxide intermediate derived from L-quebrachitol [J].
Chida, N ;
Sakata, N ;
Murai, K ;
Tobe, T ;
Nagase, T ;
Ogawa, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (01) :259-272
[8]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[9]   A METHOD FOR THE SELECTIVE OXIDATION OF 1,4-DIOLS TO LACTOLS [J].
COREY, EJ ;
PALANI, A .
TETRAHEDRON LETTERS, 1995, 36 (20) :3485-3488
[10]   THE RHODIUM CARBENOID ROUTE TO CYCLIC ETHERS - SYNTHESIS OF THE CIS-2,7-DISUBSTITUTED OXEPANE SKELETON OF ISOLAUREPINNACIN [J].
DAVIES, MJ ;
MOODY, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :9-12