Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

被引：38

作者：

Bardaji, Gisela G. ^{[1
]}

Canto, Mariona ^{[1
]}

Alibes, Ramon ^{[1
]}

Bayon, Pau ^{[1
]}

Busque, Felix ^{[1
]}

de March, Pedro ^{[1
]}

Figueredo, Marta ^{[1
]}

Font, Josep ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期

关键词：

D O I：

10.1021/jo801470u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.

引用

页码：7657 / 7662

页数：6

共 40 条

[1] An effective enantioselective approach to the securinega alkaloids:: Total synthesis of (-)-norsecurinine [J].

Alibés, R ;

Bayón, P ;

de March, P ;

Figueredo, M ;

Font, J ;

García-García, E ;

González-Gálvez, D .

ORGANIC LETTERS, 2005, 7 (22) :5107-5109

[2] A new general access to either type of Securinega alkaloids:: Synthesis of securinine and (-)-allonorsecurinine [J].

Alibés, R ;

Ballbé, M ;

Busqué, F ;

de March, P ;

Elias, L ;

Figueredo, M ;

Font, J .

ORGANIC LETTERS, 2004, 6 (11) :1813-1816

[3] LIGNANS AND LACTONES FROM PHYLLANTHUS-ANISOLOBUS [J].

BACHMANN, TL ;

GHIA, F ;

TORSSELL, KBG .

PHYTOCHEMISTRY, 1993, 33 (01) :189-191

[4]

Bayón P, 2005, TARG HETEROCYCL SYST, V9, P281

[5]

BEVAN CWL, 1964, CHEM IND-LONDON, P2054

[6] Vinylogous Mannich reactions: Some theoretical studies on the origins of diastereoselectivity [J].

Bur, SK ;

Martin, SF .

ORGANIC LETTERS, 2000, 2 (22) :3445-3447

[7] From p-benzoquinone to cyclohexane chirons:: first asymmetric synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide [J].

Busqué, F ;

Cantó, M ;

de March, P ;

Figueredo, M ;

Font, J ;

Rodríguez, S .

TETRAHEDRON-ASYMMETRY, 2003, 14 (14) :2021-2032

[8] FIRST PREPARATION OF OPTICALLY PURE KETALS OF P-BENZOQUINONE [J].

DEMARCH, P ;

ESCODA, M ;

FIGUEREDO, M ;

FONT, J ;

ALVAREZLARENA, A ;

PINIELLA, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3895-3897

[9] A facile preparation of enecarbamates [J].

Dieter, RK ;

Sharma, RR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4180-4184

[10] BIOGENESIS-LIKE TRANSFORMATION OF SALIDROSIDE TO RENGYOL AND ITS RELATED CYCLOHEXYLETHANOIDS OF FORSYTHIA-SUSPENSA [J].

ENDO, K ;

SEYA, K ;

HIKINO, H .

TETRAHEDRON, 1989, 45 (12) :3673-3682

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