cis-Decahydroquinolines via Asymmetric Organocatalysis: Application to the Total Synthesis of Lycoposerramine Z

被引：48

作者：

Bradshaw, Ben ^{[1
]}

Luque-Corredera, Carlos ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Lab Quim Organ, IBUB, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 02期

关键词：

CASCADE REACTIONS; ALKALOIDS; OXIDATION; ALDEHYDES; NITRONES;

D O I：

10.1021/ol303257y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of the Lycopodium alkaloid lycoposerramine Z is reported. Key to the strategy is a one-pot organocatalyzed Michael reaction followed by a domino Robinson annulation/intramolecular aza-Michael reaction promoted by LiON, leading to enantiopure cis-decahydroquinolines.

引用

页码：326 / 329

页数：4

共 38 条

[1] A Practical Synthetic Route to Enantiopure 6-Substituted cis-Decahydroquinolines [J].

Amat, Mercedes ;

Navio, Laura ;

Llor, Nuria ;

Molins, Elies ;

Bosch, Joan .

ORGANIC LETTERS, 2012, 14 (01) :210-213

[2] PROTON MAGNETIC-RESONANCE STUDIES OF CYCLIC COMPOUNDS .8. CONFORMATIONS OF CIS-DECAHYDROQUINOLINES AND TRANS-DECAHYDROQUINOLINES AND THEIR ACYL DERIVATIVES [J].

BOOTH, H ;

BOSTOCK, AH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (05) :615-&

[3]

Borregan M., 2009, THESIS U BARCELONA S

[4] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].

BROOKS, DW ;

LU, LDL ;

MASAMUNE, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74

[5] Aloperine: Stereocontrolled synthesis of two stereoisomers and determination of absolute configuration [J].

Brosius, AD ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :440-441

[6] A simple asymmetric organocatalytic approach to optically active cyclohexenones [J].

Carlone, Armando ;

Marigo, Mauro ;

North, Chris ;

Landa, Aitor ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2006, (47) :4928-4930

[7]

CARPINO LA, 1978, J CHEM SOC CHEM COMM, P358, DOI 10.1039/c39780000358

[8] Total synthesis of eudesmane terpenes: cyclase phase [J].

Chen, Ke ;

Ishihara, Yoshihiro ;

Galan, Maria Moron ;

Baran, Phil S. .

TETRAHEDRON, 2010, 66 (26) :4738-4744

[9] Highly efficient synthesis of methyl-substituted conjugate cyclohexenones [J].

Chong, BD ;

Ji, YI ;

Oh, SS ;

Yang, JD ;

Baik, W ;

Koo, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9323-9325

[10] Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine [J].

Comins, DL ;

Libby, AH ;

Al-awar, RS ;

Foti, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2184-2185

← 1 2 3 4 →