Total synthesis of the proposed structure of brevenal

被引:59
作者
Fuwa, Haruhiko [1 ]
Ebine, Makoto [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
D O I
10.1021/ja062524q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total synthesis of the proposed structure of brevenal, a natural marine polycyclic ether product, has been accomplished. The synthesis features (i) convergent synthesis of the pentacyclic polyether skeleton using our developed Suzuki-Miyaura coupling strategy and (ii) construction of the multi-substituted dienal side chain by CuTC-mediated Stille reaction. Comparison of the NMR data of the synthetic compound with those reported for the natural product revealed that the proposed structure of brevenal needs to be revised. Copyright © 2006 American Chemical Society.
引用
收藏
页码:9648 / 9650
页数:3
相关论文
共 37 条
[1]   Airway responses to aerosolized brevetoxins in an animal model of asthma [J].
Abraham, WM ;
Bourdelais, AJ ;
Sabater, JR ;
Ahmed, A ;
Lee, TA ;
Serebriakov, I ;
Baden, DG .
AMERICAN JOURNAL OF RESPIRATORY AND CRITICAL CARE MEDICINE, 2005, 171 (01) :26-34
[2]   Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].
Allred, GD ;
Liebeskind, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749
[3]   A new polyether ladder compound produced by the dinoflagellate Karenia brevis [J].
Bourdelais, AJ ;
Jacocks, HM ;
Wright, JLC ;
Bigwarfe, PM ;
Baden, DG .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (01) :2-6
[4]   Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays [J].
Bourdelais, AJ ;
Campbell, S ;
Jacocks, H ;
Naar, J ;
Wright, JLC ;
Carsi, J ;
Baden, DG .
CELLULAR AND MOLECULAR NEUROBIOLOGY, 2004, 24 (04) :553-563
[5]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[6]  
2-N
[7]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[8]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
[9]   THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES [J].
FLEMING, I ;
NEWTON, TW ;
ROESSLER, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2527-2532
[10]   Total synthesis of (-)-gambierol [J].
Fuwa, H ;
Kainuma, N ;
Tachibana, K ;
Sasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14983-14992