Asymmetric Synthesis of (-)-1-hydroxyquinolizidinone, a common intermediate for the syntheses of (-)-homopumiliotoxin 223G and (-)-epiquinamide

被引:52
作者
Voituriez, Arnaud [1 ]
Ferreira, Franck [1 ]
Perez-Luna, Alejandro [1 ]
Chemla, Fabrice [1 ]
机构
[1] Univ Paris 06, Chim Organ Lab, CNRS, UMR 7611,Inst Chim Mol,FR 2769, F-75252 Paris 05, France
关键词
D O I
10.1021/ol701952y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The short and efficient asymmetric synthesis of (-)-1-hydroxyquinolizidinone was achieved in seven steps and 25.2% overall yield from readily available 5-chloropentanal. It is a key intermediate in the formal syntheses of (-)-homopumilotoxin 223G and (-)-epiquinamide.
引用
收藏
页码:4705 / 4708
页数:4
相关论文
共 35 条
[1]   Total synthesis of (+)-homopumiliotoxin 223G [J].
Aoyagi, S ;
Hasegawa, Y ;
Hirashima, S ;
Kibayashi, C .
TETRAHEDRON LETTERS, 1998, 39 (15) :2149-2152
[2]   Allenylzinc reagents:: new trends and synthetic applications [J].
Botuha, Candice ;
Chemla, Fabrice ;
Ferreira, Franck ;
Perez-Luna, Alejandro ;
Roy, Brindaban .
NEW JOURNAL OF CHEMISTRY, 2007, 31 (09) :1552-1567
[3]   High kinetic resolution in the addition of a racemic allenylzinc onto enantiopure N-tert-butanesulfinimines:: Concise synthesis of enantiopure trans-2-ethynylaziridines [J].
Chemla, F ;
Ferreira, F .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8244-8250
[4]   Diastereoselective synthesis of trans-ethynyl N-tert-butanesulfinylaziridines [J].
Chemla, F ;
Ferreira, F .
SYNLETT, 2004, (06) :983-986
[5]   Stereoselective synthesis of enantioenriched acetylenic 1,2-amino alcohols [J].
Chemla, Fabrice ;
Ferreira, Franck ;
Gaucher, Xavier ;
Palais, Laetitia .
SYNTHESIS-STUTTGART, 2007, (08) :1235-1241
[6]   Synthesis of diastereoenriched acetylenic α-N-tert-butanesulfinamidoalkyl methoxymethyl ethers [J].
Chemla, Fabrice ;
Ferreira, Franck .
SYNLETT, 2006, (16) :2613-2616
[7]   A versatile approach to 6-substituted-5-methoxy-8-lactam framework and application to the formal synthesis of (±)-homopumiliotoxin 223G [J].
Chen, BF ;
Tasi, MR ;
Yang, CY ;
Chang, JK ;
Chang, NC .
TETRAHEDRON, 2004, 60 (45) :10223-10231
[8]   The addition of 2-tert-butyldimethylsilyloxyfuran to cyclic N-acyliminium ions containing cyclohexyl-based chiral auxiliaries [J].
D'Oca, MGM ;
Pilli, RA ;
Vencato, I .
TETRAHEDRON LETTERS, 2000, 41 (50) :9709-9712
[9]   Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds [J].
Daly, JW ;
Spande, TF ;
Garraffo, HM .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1556-1575
[10]   Nicotinic agonists, antagonists, and modulators from natural sources [J].
Daly, JW .
CELLULAR AND MOLECULAR NEUROBIOLOGY, 2005, 25 (3-4) :513-552