A divergent approach to the myriaporones and tedanolide: Enantioselective preparation of the common intermediate

被引：51

作者：

Taylor, RE ^{[1
]}

Ciavarri, JP ^{[1
]}

Hearn, BR ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 51期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)02110-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tedanolide and myriaporone classes of natural products represent interesting targets for synthesis because of their structural similarity and biological activity. The asymmetric preparation of a potential common intermediate in the total synthesis of each of these targets is presented. The key step, a Zr-mediated allylation, allows for the efficient preparation of the hydroxypropionate structural unit. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9361 / 9364

页数：4

共 19 条

[1]

Anh N.T., 1980, TOP CURR CHEM, V88, P145

[2] THE REACTION OF THIONYL CHLORIDE WITH ALLYLIC ALCOHOLS [J].

CASERIO, FF ;

DENNIS, GE ;

DEWOLFE, RH ;

YOUNG, WG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (15) :4182-4183

[3] DIASTEREOSELECTIVE REACTIONS OF DELTA-SILOXYALLYLZIRCONIUM REAGENTS WITH ALDEHYDES [J].

CLARK, AJ ;

KASUJEE, I ;

PEACOCK, JL .

TETRAHEDRON LETTERS, 1995, 36 (39) :7137-7140

[4] BIOACTIVE MARINE METABOLITES .35. CYTOTOXIC METABOLITES OF THE MARINE SPONGE MYCALE-ADHAERENS LAMBE [J].

FUSETANI, N ;

SUGAWARA, T ;

MATSUNAGA, S ;

HIROTA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4971-4974

[5]

HEARN BR, UNPUB

[6] FURTHER DEVELOPMENTS IN NONENZYMIC BIOGENETIC-LIKE STEROID SYNTHESIS [J].

JOHNSON, WS ;

LI, TT ;

HARBERT, CA ;

BARTLETT, WR ;

HERRIN, TR ;

STASKUN, B ;

RICH, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (14) :4461-&

[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[8] Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters [J].

Liu, JF ;

Abiko, A ;

Pei, ZH ;

Buske, DC ;

Masamune, S .

TETRAHEDRON LETTERS, 1998, 39 (14) :1873-1876

[9] ALDOL METHODOLOGY - SYNTHESIS OF VERSATILE INTERMEDIATES - 3-HYDROXY-2-VINYLCARBONYL COMPOUNDS [J].

MASAMUNE, S ;

KAIHO, T ;

GARVEY, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5521-5523

[10] Synthetic studies of 18-membered anti-tumor macrolide, tedanolide. Computer-aided conformational design of a seco-acid derivative for efficient macrolactonization [J].

Matsushima, T ;

Horita, K ;

Nakajima, N ;

Yonemitsu, O .

TETRAHEDRON LETTERS, 1996, 37 (03) :385-388

← 1 2 →