Synthesis of the C1-C26 northern portion of azaspiracid-1: Kinetic versus thermodynamic control of the formation of the bis-spiroketal

被引：35
作者：
Zhou, XT [1 ]
Carter, RG [1 ]
机构：
[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 11期
关键词：
azaspiracid-1; fused-ring systems; natural products; spiro compounds;
D O I：
10.1002/anie.200503733
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
North-South divide: An efficient synthesis of the entire C1-C26 (northern) portion of azaspiracid-1 is disclosed (see picture). Key transformations include the formation of a bis-spiroketal, the oxidation of a sulfone at C10 to form a β,γ-unsaturated ketone, a tandem Wadsworth-Emmons/hetero-Michael addition to construct ring D, and the highly selective hydroxylation at C20. (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：1787 / 1790
页数：4
相关论文
共 47 条
[1]   Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: Entry to the F-G ring system of the azaspiracids [J].
Aiguade, J ;
Hao, JL ;
Forsyth, CJ .
ORGANIC LETTERS, 2001, 3 (07) :979-982
[2]   Biomimetic studies towards the C28-C40 polycyclic domain of the azaspiracids [J].
Aiguade, J ;
Hao, JL ;
Forsyth, CJ .
TETRAHEDRON LETTERS, 2001, 42 (05) :817-820
[3]  
[Anonymous], 2001, ANGEW CHEM, V113, P3775
[4]   Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction):: scope and asymmetric applications [J].
Bourland, TC ;
Carter, RG ;
Yokochi, AFT .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (09) :1315-1329
[5]  
BUSZEK KR, 2001, 221 NAT ACS M
[6]  
BUSZEK KR, 2003, 226 ACS NAT M NEW YO
[7]   Controlling influences in bisspiroketal formation: synthesis of the ABC ring system of azaspiracid [J].
Carter, RG ;
Bourland, TC ;
Zhou, XT ;
Gronemeyer, MA .
TETRAHEDRON, 2003, 59 (45) :8963-8974
[8]   Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization [J].
Carter, RG ;
Bourland, TC ;
Graves, DE .
ORGANIC LETTERS, 2002, 4 (13) :2177-2179
[9]   Synthesis of the ABC ring system of azaspiracid.: 2.: A systematic study into the effect of C16 and C17 substitution on bis-spirocyclization [J].
Carter, RG ;
Graves, DE ;
Gronemeyer, MA ;
Tschumper, GS .
ORGANIC LETTERS, 2002, 4 (13) :2181-2184
[10]   Studies directed toward the total synthesis of azaspiracid:: Stereoselective construction of C1-C12, C13-C19, and C21-C25 fragments [J].
Carter, RG ;
Weldon, DJ .
ORGANIC LETTERS, 2000, 2 (24) :3913-3916
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