Synthesis of the C1-C17 macrolactone of tedanolide

被引：30

作者：

Hassfeld, J ^{[1
]}

Eggert, U ^{[1
]}

Kalesse, M ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2005年 / 07期

关键词：

aldol reactions; macrocycles; mitsunobu; tedanolide; total synthesis;

D O I：

10.1055/s-2005-865302

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The vinylogous Mukaiyama aldol reaction is a useful method to build up complex polyketide structures. It is successfully employed in the synthesis of the C1-C17 macrolactone of tedanolide, a highly cytotoxic marine natural product. These studies present a practical approach toward the total synthesis of tedanolide; it is pursued using the appropriate C13-C23 segment that is introduced by a pivotal aldol reaction to join both hemispheres.

引用

页码：1183 / 1199

页数：17

共 118 条

[1]

[Anonymous], 1994, ANGEW CHEM, V106, P220

[2]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[3]

2-E

[4]

Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8

[5]

Baumhof P, 2001, ANGEW CHEM INT EDIT, V40, P3672, DOI 10.1002/1521-3773(20011001)40:19<3672::AID-ANIE3672>3.0.CO

[6]

2-Y

[7] Aqua, alcohol, and acetonitrile adducts of tris(perfluorophenyl)borane: Evaluation of Bronsted acidity and ligand lability with experimental and computational methods [J].

Bergquist, C ;

Bridgewater, BM ;

Harlan, CJ ;

Norton, JR ;

Friesner, RA ;

Parkin, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10581-10590

[8] 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

[9] Catalytic asymmetric access to α,β unsaturated δ-lactones through a vinylogous aldol reaction:: Application to the total synthesis of the Prelog-Djerassi lactone [J].

Bluet, G ;

Bazán-Tejeda, B ;

Campagne, JM .

ORGANIC LETTERS, 2001, 3 (23) :3807-3810

[10] Catalytic Asymmetric Vinylogous Mukaiyama-aldol (CAVM) reactions: The enolate activation [J].

Bluet, G ;

Campagne, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4293-4298

← 1 2 3 4 5 6 7 8 9 10 →