Controlling influences in bisspiroketal formation: synthesis of the ABC ring system of azaspiracid

被引:19
作者
Carter, RG [1 ]
Bourland, TC [1 ]
Zhou, XT [1 ]
Gronemeyer, MA [1 ]
机构
[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
基金
美国国家卫生研究院;
关键词
azaspiracid; bisspiroketal; bisspirocyclization; Julia coupling; substituent effects; anomeric effect;
D O I
10.1016/j.tet.2003.03.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substitution effects on the stereochemical outcome of bisspiroketalization on the C-1-C-17 carbon backbone of azaspiracid is presented. A possible explanation is offered to explain the observed stereochemical outcome. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8963 / 8974
页数:12
相关论文
共 52 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]   Synthesis of the bis-spiroacetal moiety of the polyether antibiotic CP44,161 [J].
Allen, PR ;
Brimble, MA ;
Prabaharan, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04) :379-389
[4]   SYNTHESES WITH SULFONES .49. STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-3,9-DIMETHYL 6-(1-METHYLETHYL) (E)-5,8-DECADIEN-1-OL ACETATE, SEXUAL PHEROMONE OF YELLOW SCALE [J].
ALVAREZ, E ;
CUVIGNY, T ;
DUPENHOAT, CH ;
JULIA, M .
TETRAHEDRON, 1988, 44 (01) :119-126
[5]   USEFUL NEW ACYL ANION EQUIVALENTS USING OXIRANYL PHENYL SULFONES [J].
ASHWELL, M ;
JACKSON, RFW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :835-836
[7]   SYNTHESIS OF TRANS-14-PHENYLSULFONYL-1,7,9-TRIOXADISPIRO[5.1.5.3]HEXADECANE AND CIS-14-PHENYLSULFONYL-1,7,9-TRIOXADISPIRO[5.1.5.3]HEXADECANE [J].
BRIMBLE, MA ;
RUSH, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :497-500
[8]   Synthesis of bis-spiroacetal ring systems [J].
Brimble, MA ;
Farès, FA .
TETRAHEDRON, 1999, 55 (25) :7661-7706
[9]  
BUSZEK KR, 221 NAT ACS M SAN DI
[10]   Synthesis of the novel 1,7,9-trioxadispiro(4.1.5.2]-tetradecane ring system present in the spirolides [J].
Caprio, V ;
Brimble, MA ;
Furkert, DP .
TETRAHEDRON, 2001, 57 (18) :4023-4034