Reaction Development Utilizing the Features of Chemical Elements and Synthesis of Marine Natural Products

被引:0
作者
Saito, Tatsuo [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
来源
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN | 2018年 / 138卷 / 11期
基金
日本学术振兴会;
关键词
rhenium catalysis; 1,3-transposition; polyether; maitotoxin; gold catalysis; C'D'E'F'-RING-SYSTEM; BREVETOXIN-B; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL-ACTIVITY; ALLYLIC ALCOHOLS; CONVERGENT SYNTHESIS; MAITOTOXIN; COMPLEXES; ISOMERIZATION; ASSIGNMENTS;
D O I
10.1248/yakushi.18-00126
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Marine natural products and biologically active compounds often contain cyclic ether units. Thus, regio- and stereoselective construction of these structures has long been a topic of interest in organic synthesis. This review summarizes new synthetic approaches to polycyclic ether natural products utilizing the features of chemical elements.
引用
收藏
页码:1335 / 1344
页数:10
相关论文
共 42 条
[1]   Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes [J].
Bellemin-Laponnaz, S ;
Le Ny, JP ;
Osborn, JA .
TETRAHEDRON LETTERS, 2000, 41 (10) :1549-1552
[2]   Metal oxo complexes as catalysts for the isomerisation of allylic alcohols [J].
Bellemin-Laponnaz, S ;
Le Ny, JP .
COMPTES RENDUS CHIMIE, 2002, 5 (04) :217-224
[3]   Mechanistic insights into the very efficient [ReO3OSiR3]-catalyzed isomerization of allyl alcohols [J].
Bellemin-Laponnaz, S ;
Gisie, H ;
LeNy, JP ;
Osborn, JA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (09) :976-978
[4]   Gold Catalysis: Hydrolysis of Di(alkoxy)carbenium Ion Intermediates as a Sensor for the Electronic Properties of Gold(I) Complexes [J].
Doepp, Rene ;
Lothschuetz, Christian ;
Wurm, Thomas ;
Pernpointner, Markus ;
Keller, Sascha ;
Rominger, Frank ;
Hashmi, A. Stephen K. .
ORGANOMETALLICS, 2011, 30 (21) :5894-5903
[5]   Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].
Dorel, Ruth ;
Echavarren, Antonio M. .
CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072
[6]   Regio- and Stereocontrol in Rhenium-Catalyzed Transposition of Allylic Alcohols [J].
Herrmann, Aaron T. ;
Saito, Tatsuo ;
Stivala, Craig E. ;
Tom, Janine ;
Zakarian, Armen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5962-+
[7]   1,3-transposition of allylic alcohols catalyzed by methyltrioxorhenium [J].
Jacob, J ;
Espenson, JH ;
Jensen, JH ;
Gordon, MS .
ORGANOMETALLICS, 1998, 17 (09) :1835-1840
[8]   Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities [J].
Kadota, I ;
Takamura, H ;
Sato, K ;
Ohno, A ;
Matsuda, K ;
Satake, M ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11893-11899
[9]   Total synthesis of gambierol [J].
Kadota, I ;
Takamura, H ;
Sato, K ;
Ohno, A ;
Matsuda, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :46-47
[10]   A simple and practical method for the stereoselective synthesis of (Z)-1-iodo-1-alkenes from 1,1-diiodo-1-alkenes [J].
Kadota, I ;
Ueno, H ;
Ohno, A ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 2003, 44 (48) :8645-8647