Efficient synthesis of the C1-C11 fragment of the tedanolides.: The nonaldol aldol process in synthesis

被引：51

作者：

Jung, ME ^{[1
]}

Marquez, R ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 12期

关键词：

D O I：

10.1021/ol005675l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

引用

页码：1669 / 1672

页数：4

共 29 条

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

KATSUKI, T ;

SHARPLESS, KB .

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

[12] 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

[13] KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].

MARTIN, VS ;

WOODARD, SS ;

KATSUKI, T ;

YAMADA, Y ;

IKEDA, M ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240

[14] 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

[15]

Matsushima T, 1998, CHEM PHARM BULL, V46, P1335

[16]

Matsushima T, 1999, CHEM PHARM BULL, V47, P308

[17]

Matsushima T, 1999, SYNLETT, P780

[18]

MIHAILOVIC ML, 1985, J SERB CHEM SOC, V50, P5

[19] HALONIUM-INITIATED CYCLIZATIONS OF ALLYLIC URETHANES - STEREOSELECTIVITY AND REGIOSELECTIVITY IN FUNCTIONALIZING THE OLEFINIC BOND [J].

PARKER, KA ;

OFEE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :654-655

[20] ASYMMETRIC EPOXIDATION PROVIDES SHORTEST ROUTES TO 4 CHIRAL EPOXY ALCOHOLS WHICH ARE KEY INTERMEDIATES IN SYNTHESES OF METHYMYCIN, ERYTHROMYCIN, LEUKOTRIENE C-1, AND DISPARLURE [J].

ROSSITER, BE ;

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) :464-465

← 1 2 3 →