Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment

被引：40

作者：

Loh, TP ^{[1
]}

Feng, LC ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(01)00401-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C(13)C(23) subunit of tedanolide was obtained using a boron-mediated aldol reaction as the key step to control the C-16, and C-17, stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3223 / 3226

页数：4

共 22 条

[1] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].

CHEN, KM ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1987, 28 (02) :155-158

[2] TOTAL SYNTHESES OF (+)-THYRSIFEROL, (+)-THYRSIFERYL 2O-ACETATE, AND (+)-VENUSTATRIOL [J].

HASHIMOTO, M ;

KAN, T ;

NOZAKI, K ;

YANAGIYA, M ;

SHIRAHAMA, H ;

MATSUMOTO, T .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5088-5107

[3] AN EFFICIENT ROUTE TO A KEY A-RING SYNTHON FOR 1-ALPHA,25-DIHYDROXYVITAMIN D-3 AND ITS ANALOGS [J].

HATAKEYAMA, S ;

IRIE, H ;

SHINTANI, T ;

NOGUCHI, Y ;

YAMADA, H ;

NISHIZAWA, M .

TETRAHEDRON, 1994, 50 (47) :13369-13376

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

Jung, ME ;

Marquez, R .

ORGANIC LETTERS, 2000, 2 (12) :1669-1672

[5] Use of the non-aldol aldol process in the synthesis of the C1-C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans [J].

Jung, ME ;

Lee, CP .

TETRAHEDRON LETTERS, 2000, 41 (50) :9719-9723

[6] 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

[7]

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

[8] 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

[9]

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

[10]

Matsushima T, 1999, SYNLETT, P780

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