Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies

被引：359

作者：

Aho, JE ^{[1
]}

Pihko, PM ^{[1
]}

Rissa, TK ^{[1
]}

机构：

[1] Aalto Univ, Organ Chem Lab, FI-02015 Helsinki, Finland

来源：

CHEMICAL REVIEWS | 2005年 / 105卷 / 12期

关键词：

D O I：

10.1021/cr050559n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An overview of the synthetic challenges associated with non-anomeric spiroketals, a functional assembly found in polyether antibiotics, marine natural products and insect pheromones, is given. Focus is on nanomeric [6,5]-spiroketals, [6,6]-spiroketals and tricyclic spiroketals. Conformational locking, a requirement for the stabilization of nanomeric structures, is described. Furthermore, general strategies for the synthesis of nanomeric spiroketals are outlined.

引用

收藏

页码：4406 / 4440

页数：35

相关论文

共 249 条

[1] Synthesis of C-2 functionalised 1,6,8-trioxadispiro[4.1.5.3]pentadec-13-enes [J].

Allen, PR ;

Brimble, MA ;

Fares, FA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2403-2411

[2]

ALLEN PR, 1999, J CHEM SOC P1, P295

[3]

Amano S, 1997, SYNLETT, P1300

[4] Medicinal chemistry of neuronal voltage-gated sodium channel blockers [J].

Anger, T ;

Madge, DJ ;

Mulla, M ;

Riddall, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (02) :115-137

[5]

ANTEUNIS MJO, 1977, B SOC CHIM BELG, V86, P609

[6]

ASAKURA D, 2000, SYNLETT, P1733

[7] Synthesis of the JKLM-ring fragment of ciguatoxin [J].

Baba, T ;

Huang, G ;

Isobe, M .

TETRAHEDRON, 2003, 59 (35) :6851-6872

[8] DETERMINATION OF THE STEREOCHEMISTRY OF 2,2-DIMETHYL-1,6,8-TRIOXADISPIRO(4.1.5.3)PENTADEC-13-ENE FORMED BY 2 SEQUENTIAL CYCLIZATION REACTIONS USING HIGH-FIELD H-1-NMR SPECTROSCOPY [J].

BAKER, R ;

BRIMBLE, MA ;

ROBINSON, JA .

TETRAHEDRON LETTERS, 1985, 26 (17) :2115-2118

[9] IDENTIFICATION AND SYNTHESIS OF THE MAJOR SEX-PHEROMONE OF THE OLIVE FLY (DACUS-OLEAE) [J].

BAKER, R ;

HERBERT, R ;

HOWSE, PE ;

JONES, OT ;

FRANCKE, W ;

REITH, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (02) :52-53

[10] ISOLATION AND SYNTHESIS OF 3-HYDROXY-1 AND 4-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANES FROM THE OLIVE FLY (DACUS-OLEAE) [J].

BAKER, R ;

HERBERT, RH ;

PARTON, AH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) :601-603

← 1 2 3 4 5 6 7 8 9 10 →