Advances in the vinylogous Mukaiyama aldol reaction and its application to the synthesis of the C1-C7 subunit of oleandolide

被引：23

作者：

Hassfeld, J ^{[1
]}

Kalesse, M ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(02)00993-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a stereo pentacle of the macrolide antibiotic oleandolide is reported. The C1-C7 fragment resembles the analogous segment of Panek's total synthesis of oleandolide. The use of the vinylogous Mukaiyama aldol reaction shortens the route significantly and has the advantage of utilizing an easily accessible ketene acetal. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5093 / 5095

页数：3

共 12 条

[1] The first total synthesis of (+)-ratjadone [J].

Bhatt, U ;

Christmann, M ;

Quitschalle, M ;

Claus, E ;

Kalesse, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1885-1893

[2] MACROLIDE STEREOCHEMISTRY .I. TOTAL ABSOLUTE CONFIGURATION OF OLEANDOMYCIN [J].

CELMER, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (08) :1797-&

[3] Vinylogous Mukaiyama aldol reactions with triarylboranes [J].

Christmann, M ;

Kalesse, M .

TETRAHEDRON LETTERS, 2001, 42 (07) :1269-1271

[4] General strategies toward the syntheses of macrolide antibiotics. The total syntheses of 6-deoxyerythronolide B and oleandolide [J].

Evans, DA ;

Kim, AS ;

Metternich, R ;

Novack, VJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :5921-5942

[5] Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions [J].

Hassfeld, J ;

Christmann, M ;

Kalesse, M .

ORGANIC LETTERS, 2001, 3 (22) :3561-3564

[6] THE STRUCTURE OF OLEANDOMYCIN [J].

HOCHSTEIN, FA ;

ELS, H ;

CELMER, WD ;

SHAPIRO, BL ;

WOODWARD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (12) :3225-3227

[7] Total synthesis of oleandolide [J].

Hu, T ;

Takenaka, N ;

Panek, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9229-9230

[8] STEREOCHEMISTRY OF MACROLIDES .3. X-RAY CRYSTAL-STRUCTURE ANALYSIS OF 11,4''-BIS[O-(PARA-BROMOBENZOYL)]OLEANDOMYCIN [J].

OGURA, H ;

FURUHATA, K ;

HARADA, Y ;

IITAKA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (21) :6733-6737

[9] STUDIES IN MACROLIDE SYNTHESIS - A STEREOCONTROLLED SYNTHESIS OF OLEANDOLIDE EMPLOYING REAGENT-CONTROLLED AND SUBSTRATE-CONTROLLED ALDOL REACTIONS OF (S)-1-(BENZYLOXY)-2-METHYLPENTAN-3-ONE [J].

PATERSON, I ;

NORCROSS, RD ;

WARD, RA ;

ROMEA, P ;

LISTER, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11287-11314

[10]

SOBIN BA, 1955, ANTIBIOT ANNU, V2, P827

← 1 2 →