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
[11]   Synthesis of an Advanced Maoecrystal V Core Structure [J].
Dong, Lin ;
Deng, Lujiang ;
Lim, Yee Hwee ;
Leung, Gulice Y. C. ;
Chen, David Y. -K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) :5778-5781
[12]  
Fairweather K. A., 2006, ORG LETT, V8, P3395
[13]   Highly active and selective catalysts for the formation of α-aryl ketones [J].
Fox, JM ;
Huang, XH ;
Chieffi, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370
[14]   Total Synthesis of (±) Maoecrystal V [J].
Gong, Jianxian ;
Lin, Guang ;
Sun, Wenbo ;
Li, Chuang-Chuang ;
Yang, Zhen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) :16745-16746
[15]   Synthetic Study toward the Total Synthesis of Maoecrystal V [J].
Gong, Jianxian ;
Lin, Guang ;
Li, Chuang-chuang ;
Yang, Zhen .
ORGANIC LETTERS, 2009, 11 (21) :4770-4773
[16]   Studies toward the Synthesis of Maoecrystal V [J].
Gu, Zhenhua ;
Zakarian, Armen .
ORGANIC LETTERS, 2011, 13 (05) :1080-1082
[17]   An economical and convenient synthesis of vinyl sulfones [J].
Guan, Zheng-Hui ;
Zuo, Wei ;
Zhao, Lian-Biao ;
Ren, Zhi-Hui ;
Liang, Yong-Min .
SYNTHESIS-STUTTGART, 2007, (10) :1465-1470
[18]   A novel chiral super-Lewis acidic catalyst for enantioselective synthesis [J].
Hayashi, Y ;
Rohde, JJ ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5502-5503
[19]   SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].
HOVEYDA, AH ;
EVANS, DA ;
FU, GC .
CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370
[20]   Syntheses of biologically active natural products and leading compounds for new pharmaceuticals employing effective construction of a polycyclic skeleton [J].
Ihara, Masataka .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (06) :765-774