Synthesis of (+)-Muricatacin and a Formal Synthesis of CMI-977 from L-Malic Acid

被引：7

作者：

Gonzalez, Maria ^{[1
]}

Gandara, Zoila ^{[1
]}

Martinez, Andrea ^{[1
]}

Gomez, Generosa ^{[1
]}

Fall, Yagamare ^{[1
]}

机构：

[1] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36310, Spain

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 12期

关键词：

butenolide; oxygen; natural products; total synthesis; oxidation; CONCISE TOTAL-SYNTHESIS; FURAN APPROACH; STEREOSELECTIVE-SYNTHESIS; CHIRAL TETRAHYDROFURANS; SECONDARY ALCOHOLS; GAMMA-LACTONES; (-)-MURICATACIN; OXACYCLES; MURICATACIN; ANALOGS;

D O I：

10.1055/s-0033-1338934

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-muricatacin and a formal synthesis of CMI-977 have been achieved using commercially available L-malic acid based on our furan approach to oxacyclic systems, the proven scope of which is thus broadened.

引用

页码：1693 / 1700

页数：8

共 31 条

[1] De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates [J].

Ahmed, Md. Moinuddin ;

Cui, Hu ;

O'Doherty, George A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6686-6689

[2] The furan approach to oxacycles.: Part 3:: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans [J].

Alonso, D ;

Pérez, M ;

Gómez, G ;

Covelo, B ;

Fall, Y .

TETRAHEDRON, 2005, 61 (08) :2021-2026

[3] Synthesis of Enantiomerically Pure 2,5-Disubstituted 3-Oxygenated Tetrahydrofurans [J].

Alvarez, Carla ;

Perez, Manuel ;

Zuniga, Andrea ;

Gomez, Generosa ;

Fall, Yagamare .

SYNTHESIS-STUTTGART, 2010, (22) :3883-3890

[4] THE INVENTION OF RADICAL REACTIONS .24. RELATIVE RATES OF ACYLATION AND RADICAL DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

DORCHAK, J ;

JASZBERENYI, JC .

TETRAHEDRON, 1992, 48 (36) :7435-7446

[5] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[6] Stereoselective synthesis of polytetrahydropyrans [J].

Canoa, Pilar ;

Vega, Nuria ;

Perez, Manuel ;

Gomez, Generosa ;

Fall, Yagamare .

TETRAHEDRON LETTERS, 2008, 49 (07) :1149-1151

[7] The furan approach to oxacycles.: Part 6:: From THF to fused polyoxepanes [J].

Canoa, Pilar ;

Perez, Manuel ;

Covelo, Berta ;

Gomez, Generosa ;

Fall, Yagamare .

TETRAHEDRON LETTERS, 2007, 48 (19) :3441-3443

[8] The Furan Approach to Oxacycles: New Entry to the Synthesis of Isodideoxynucleosides [J].

Canoa, Pilar ;

Gandara, Zoila ;

Perez, Manuel ;

Gago, Rafael ;

Gomez, Generosa ;

Fall, Yagamare .

SYNTHESIS-STUTTGART, 2011, (03) :431-436

[9] Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues [J].

Cave, A ;

Chaboche, C ;

Figadere, B ;

Harmange, JC ;

Laurens, A ;

Peyrat, JF ;

Pichon, M ;

Szlosek, M ;

CotteLafitte, J ;

Quero, AM .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (7-8) :617-623

[10] Synthesis of seven-membered oxacycles.: Part 2:: The furan approach [J].

Fall, Y ;

Vidal, B ;

Alonso, D ;

Gómez, G .

TETRAHEDRON LETTERS, 2003, 44 (24) :4467-4469

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