Aldol condensation reactions of tricarbonyliron complexes. Towards building blocks for the synthesis of carbomycin B/tylosin macrolide antibiotics and fluorinated analogs

被引：7

作者：

Franck-Neumann, M ^{[1
]}

Geoffroy, P ^{[1
]}

Gumery, F ^{[1
]}

机构：

[1] Univ Strasbourg 1, CNRS, Lab Chim Organ Synthet, Inst Chim, F-67000 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)00569-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Tricarbonyliron complexes of alpha-methoxyheptadienone 3 and octadienone 8 were reacted as silyl enol ethers with protected beta-hydroxypropanal and TiCl4, to give the syn-syn aldol condensation products 4 and 11 as major, isolated diastereomers (61 and 45%), Products 4 and 11 were converted into key intermediates of previous total syntheses of carbonolide B and tylonide, in a few steps, including the iron-directed reduction to syn diols and partial ozonolysis. The same methodology was used for the high yielding synthesis of a monofluorinated analog. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4219 / 4222

页数：4

共 9 条

[1]

NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS [J].

COREY, EJ ;

GILMAN, NW ;

GANEM, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5616-&

[2]

Aldol condensation reactions of tricarbonyliron complexes.: Easy access to diastereomerically pure 1,2,3-trisubstituted 1,3-diols from α-substituted dienone complexes [J].

Franck-Neumann, M ;

Geoffroy, P ;

Gumery, F ;

Bissinger, P .

TETRAHEDRON LETTERS, 2000, 41 (21) :4213-4217

[3]

Aldol condensation reactions of chiral (dienone) tricarbonyliron complexes .2. Enantioselective synthesis of the dienic polyols streptenols C and D (metabolites from Streptomyces Fimbriatus). [J].

FranckNeumann, M ;

Bissinger, P ;

Geoffroy, P .

TETRAHEDRON LETTERS, 1997, 38 (25) :4469-4472

[4]

SYNTHETIC STUDIES OF RIFAMYCINS .2. SYNTHESES OF METHYL 2,4,6,7-TETRADEOXY-4-C-METHYL-3-O-METHYL-ALPHA-L-ARABINO-HEPTOPYRANOSID-6-ULOSE AND ITS DERIVATIVES UTILIZABLE IN THE CONSTRUCTION OF THE RIFAMYCIN ANSA CHAIN PORTION [J].

NAKATA, M ;

IKEYAMA, Y ;

TAKAO, H ;

KINOSHITA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (11) :3252-3258

[5]

SYNTHESIS OF 16-MEMBERED-RING MARCOLIDE ANTIBIOTICS .4. CARBOMYCIN-B AND LEUCOMYCIN-A3 - TOTAL SYNTHESIS OF CYCLIC KEY INTERMEDIATE [J].

NICOLAOU, KC ;

PAVIA, MR ;

SEITZ, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1224-1226

[6]

CARBOHYDRATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 16-MEMBERED-RING MACROLIDE ANTIBIOTICS .5. TOTAL SYNTHESIS OF O-MYCINOSYLTYLONOLIDE - SYNTHESIS OF KEY INTERMEDIATES [J].

NICOLAOU, KC ;

PAVIA, MR ;

SEITZ, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :2027-2029

[7]

OZONOLYSIS .2. THE EFFECT OF PYRIDINE ON THE OZONOLYSIS OF 4,22-STIGMASTADIEN-3-ONE [J].

SLOMP, G ;

JOHNSON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (04) :915-921

[8]

SYNTHESIS OF CARBOMYCIN-B - INTRODUCTION OF AMINO DISACCHARIDE ONTO 16-MEMBERED-RING AGLYCONE [J].

TATSUTA, K ;

TANAKA, A ;

FUJIMOTO, K ;

KINOSHITA, M ;

UMEZAWA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (17) :5826-5827

[9]

TATSUTA K, 1981, TETRAHEDRON LETT, P3997

← 1 →