Cyclative cleavage via solid-phase supported stabilized sulfur ylides: synthesis of macrocyclic lactones

被引：23

作者：

La Porta, E

Piarulli, U

Cardullo, F

Paio, A

Provera, S

Seneci, P

Gennari, C

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, Ctr CNR Studio Sostanze Organ Nat, I-20133 Milan, Italy

[2] Univ Insubria, Dipartimento Sci Chim Fis & Mat, I-22100 Como, Italy

[3] Glaxo SmithKline, Med Res Ctr, I-37135 Verona, Italy

[4] Nucleotide Analog Design AG, D-80339 Munich, Germany

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

solid-phase synthesis; macrocycles; cyclopropanes; sulfonium salts;

D O I：

10.1016/S0040-4039(01)02258-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of macrolactones bearing a cyclopropyl ring condensed to the macrocycle is reported via a cyclization-release strategy making use of solid-phase supported stabilized sulfur ylides. (C), 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：761 / 766

页数：6

共 29 条

[1] SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME DERIVATIVES OF TOLYPOMYCINONE - RELATIONSHIP BETWEEN STRUCTURE AND ACTIVITY IN ANSAMYCINS [J].

BELLOMO, P ;

BRUFANI, M ;

MARCHI, E ;

MASCELLANI, G ;

MELLONI, W ;

MONTECCHI, L ;

STANZANI, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (10) :1287-1291

[2] Stereoselective cyclopropanation of enones with ethyl dimethylsulfonium acetate bromide in the presence of DBU [J].

Collado, I ;

Dominguez, C ;

Ezquerra, J ;

Pedregal, C ;

Monn, JA .

TETRAHEDRON LETTERS, 1997, 38 (12) :2133-2136

[3] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[4] Synthesis of cyclopropane containing natural products [J].

Donaldson, WA .

TETRAHEDRON, 2001, 57 (41) :8589-8627

[5] A tandem radical macrocyclisation-transannular cyclisation approach towards the taxanes [J].

Hitchcock, SA ;

Houldsworth, SJ ;

Pattenden, G ;

Pryde, DC ;

Thomson, NM ;

Blake, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3181-3206

[6] Catalytic asymmetric synthesis of glycidic amides via chiral sulfur ylides [J].

Imashiro, R ;

Yamanaka, T ;

Seki, M .

TETRAHEDRON-ASYMMETRY, 1999, 10 (15) :2845-2851

[7] AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].

IRELAND, RE ;

LIU, LB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899

[8] Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library [J].

Kobayashi, S ;

Hachiya, I ;

Suzuki, S ;

Moriwaki, M .

TETRAHEDRON LETTERS, 1996, 37 (16) :2809-2812

[9] A new solid-phase linker for Suzuki coupling with concomitant macrocyclization:: synthesis of β-turn mimics [J].

Li, W ;

Burgess, K .

TETRAHEDRON LETTERS, 1999, 40 (36) :6527-6530

[10] Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes [J].

López-Herrera, FJ ;

Sarabia-García, F ;

Pedraza-Cebrián, GM ;

Pino-González, MS .

TETRAHEDRON LETTERS, 1999, 40 (07) :1379-1380

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