Solid phase combinatorial synthesis of a library of macro-heterocycles and related acyclic compounds

被引：14

作者：

Ramaseshan, M

Dory, YL ^{[1
]}

Deslongchamps, P

机构：

[1] Univ Sherbrooke, Dept Chim, Organ Synth Lab, Inst Pharmacol Sherbrooke, Sherbrooke, PQ J1H 5N4, Canada

[2] Univ Sherbrooke, Inst Pharmacol Sherbroke, NeoKimia Inc, Sherbrooke, PQ J1H 5N4, Canada

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/cc000030y

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A solid phase synthesis of macrolactones from three building blocks and in eight steps is described. The synthesis which is carried out on the DHP resin includes Mitsunobu and DIC couplings. The macrocyclization occurs by SN2 displacement of an allylic chloride by a malonate anion. The synthetic methodology is suitable for the synthesis of arrays of macrocycles as well as linear compounds.

引用

收藏

页码：615 / 623

页数：9

相关论文

共 17 条

[1] STUDY ON THE INFLUENCE OF UNSATURATIONS ON THE FORMATION OF C-11, C-12, C-13 AND C-14 MEMBERED RINGS [J].

BRILLON, D ;

DESLONGCHAMPS, P .

TETRAHEDRON LETTERS, 1986, 27 (10) :1131-1134

[2] Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A [J].

Defauw, JM ;

Murphy, MM ;

Jagdmann, GE ;

Hu, H ;

Lampe, JW ;

Hollinshead, SP ;

Mitchell, TJ ;

Crane, HM ;

Heerding, JM ;

Mendoza, JS ;

Davis, JE ;

Darges, JW ;

Hubbard, FR ;

Hall, SE .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5215-5227

[3]

GARGIPATI RS, 1996, J ORG CHEM, V61, P2911

[4] The biomimetic construction of fused cyclic polyethers [J].

Hayashi, N ;

Fujiwara, K ;

Murai, A .

TETRAHEDRON, 1997, 53 (37) :12425-12468

[5] A strategy for macrocyclic ring closure and functionalization aimed toward split-pool syntheses [J].

Lee, D ;

Sello, JK ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) :10648-10649

[6] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[7] RADIOFREQUENCY ENCODED COMBINATORIAL CHEMISTRY [J].

NICOLAOU, KC ;

XIAO, XY ;

PARANDOOSH, Z ;

SENYEI, A ;

NOVA, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20) :2289-2291

[8] Synthesis of epothilones A and B in solid and solution phase [J].

Nicolaou, KC ;

Winssinger, N ;

Pastor, J ;

Ninkovic, S ;

Sarabia, F ;

He, Y ;

Vourloumis, D ;

Yang, Z ;

Li, T ;

Giannakakou, P ;

Hamel, E .

NATURE, 1997, 387 (6630) :268-272

[9] TOTAL SYNTHESIS OF BIOACTIVE MARINE MACROLIDES [J].

NORCROSS, RD ;

PATERSON, I .

CHEMICAL REVIEWS, 1995, 95 (06) :2041-2114

[10]

RAMASESHAN M, IN PRESS TETRAHEDRON