Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3

被引:59
作者
Nicolaou, KC
Frederick, MO
Petrovic, G
Cole, KP
Loizidou, EZ
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
azaspiracids; fused-ring systems; natural products; spiro compounds; total synthesis;
D O I
10.1002/anie.200600295
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The 39 steps: The recently proposed revised structures of azaspiracid-2 and -3 (see picture), the two most potent members of the azaspiracid family, have been confirmed through the total syntheses of the two compounds. These 39-step syntheses represent a major improvement over the first-generation synthesis of azaspiracid-1 (50 steps). (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2609 / 2615
页数:7
相关论文
共 57 条
[51]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523
[52]   A SIMPLE METHOD OF DETHIOACETALIZATION [J].
STORK, G ;
ZHAO, K .
TETRAHEDRON LETTERS, 1989, 30 (03) :287-290
[53]  
TOLSTIKOV GA, 1989, SYNTHESIS-STUTTGART, P940
[54]  
Wessjohann LA, 1999, SYNTHESIS-STUTTGART, P1
[55]  
Zhou X.-T., 2006, ANGEW CHEM, V118, P1819
[56]   Synthesis of the C1-C26 northern portion of azaspiracid-1: Kinetic versus thermodynamic control of the formation of the bis-spiroketal [J].
Zhou, XT ;
Carter, RG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1787-1790
[57]   Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1 [J].
Zhou, XT ;
Carter, RG .
CHEMICAL COMMUNICATIONS, 2004, (19) :2138-2140