Progress towards the total synthesis of tedanolide:: an efficient assembly of the C1-C11 subunit

被引：27

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 / 34期

关键词：

D O I：

10.1016/S0040-4039(01)01169-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-1-C-11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C-6 and C-7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C-2, C-3 hydroxyl groups, selective protection of the hydroxyl group at C-2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6001 / 6005

页数：5

共 33 条

[11] Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides [J].

Jung, ME ;

Lee, CP .

ORGANIC LETTERS, 2001, 3 (03) :333-336

[12] 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

[13] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[14] 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

[15]

MASAMUNE S, 1979, TETRAHEDRON LETT, P1665

[16] 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

[17]

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

[18]

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

[19]

Matsushima T, 1999, SYNLETT, P780

[20] NEW CROSS-ALDOL REACTION VIA VINYLOXYBORANES [J].

MUKAIYAMA, T ;

INOUE, T .

CHEMISTRY LETTERS, 1976, (06) :559-562

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