The total synthesis of (+)-tedanolide

被引：50

作者：

Ehrlich, Gunnar ^{[1
]}

Hassfeld, Jorma ^{[1
]}

Eggert, Ulrike ^{[1
]}

Kalesse, Markus ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 43期

关键词：

D O I：

10.1021/ja0659572

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide. Copyright © 2006 American Chemical Society.

引用

页码：14038 / 14039

页数：2

共 42 条

[11]

JULIAN LD, 2005, THESIS U MICHIGAN

[12] 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

[13] Conversion of homoallylic alcohols with alkene protection to the corresponding methyl ketones [J].

Jung, ME ;

Karama, U ;

Marquez, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :663-665

[14] Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiary and secondary carbocationic centers [J].

Jung, ME ;

Marquez, R .

TETRAHEDRON LETTERS, 1999, 40 (16) :3129-3132

[15] 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

[16] 1,1,1,3,3,3-HEXAFLUORO-2-PROPANOL FOR THE REMOVAL OF THE 4,4'-DIMETHOXYTRITYL PROTECTING GROUP FROM THE 5'-HYDROXYL OF ACID-SENSITIVE NUCLEOSIDES AND NUCLEOTIDES [J].

LEONARD, NJ ;

NEELIMA .

TETRAHEDRON LETTERS, 1995, 36 (43) :7833-7836

[17]

LEY SV, 1994, SYNTHESIS-STUTTGART, P639

[18] 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

[19] Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment [J].

Loh, TP ;

Feng, LC .

TETRAHEDRON LETTERS, 2001, 42 (18) :3223-3226

[20] Progress towards the total synthesis of tedanolide:: an efficient assembly of the C1-C11 subunit [J].

Loh, TP ;

Feng, LC .

TETRAHEDRON LETTERS, 2001, 42 (34) :6001-6005

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