Total Synthesis of (±)-Maoecrystal V

被引:94
作者
Peng, Feng [1 ]
Danishefsky, Samuel J. [1 ,2 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10065 USA
关键词
DIELS-ALDER REACTIONS; MAOECRYSTAL-V; CHIRAL OXAZABOROLIDINE; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; EFFICIENT; OXYFUNCTIONALIZATION; REARRANGEMENT; HYDROCARBONS; CONVERSION;
D O I
10.1021/ja309905j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of racemic maoecrystal V has been accomplished. Key steps include an intramolecular Diels-Alder cyclization to rapidly construct the core system from simple starting materials and the creation of the A-C ring transfusion through intramolecular delivery of a hydrogen to the hindered beta-face of the ring system.
引用
收藏
页码:18860 / 18867
页数:8
相关论文
共 56 条
[1]   Toward the Total Synthesis of Maoecrystal V: Establishment of Contiguous Quaternary Stereocenters [J].
Baitinger, Irina ;
Mayer, Peter ;
Trauner, Dirk .
ORGANIC LETTERS, 2010, 12 (24) :5656-5659
[2]   The total synthesis of (±)-merrilactone A [J].
Birman, VB ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2080-2081
[3]   A Concise Total Synthesis of (-)-Maoecrystal Z [J].
Cha, Jacob Y. ;
Yeoman, John T. S. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (38) :14964-14967
[4]  
Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[5]  
2-B
[6]   Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine [J].
Corey, EJ ;
Shibata, T ;
Lee, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3808-3809
[7]   Oxyfunctionalization of non-natural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties [J].
D'Accolti, L ;
Dinoi, A ;
Fusco, C ;
Russo, A ;
Curci, R .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7806-7810
[8]   USE OF BETA-PHENYLSULFINYL-ALPHA,BETA-UNSATURATED CARBONYL DIENOPHILES IN DIELS-ALDER REACTIONS [J].
DANISHEFSKY, S ;
HARAYAMA, T ;
SINGH, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7008-7012
[9]   TOTAL SYNTHESIS OF DL-TAZETTINE AND 6A-EPIPRETAZETTINE - A FORMAL SYNTHESIS OF DL-PRETAZETTINE - SOME OBSERVATIONS ON THE RELATIONSHIP OF 6A-EPIPRETAZETTINE AND TAZETTINE [J].
DANISHEFSKY, S ;
MORRIS, J ;
MULLEN, G ;
GAMMILL, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) :7591-7599
[10]  
DENIS JM, 1972, SYNTH-INT J METHODS, P549