Enantioselective Total Synthesis of the Selective PI3 Kinase Inhibitor Liphagal

被引：41

作者：

Alvarez-Manzaneda, Enrique ^{[1
]}

Chahboun, Rachid ^{[1
]}

Alvarez, Esteban ^{[1
]}

Cano, M. Jose ^{[1
]}

Haidour, Ali ^{[1
]}

Alvarez-Manzaneda, Ramon ^{[2
]}

机构：

[1] Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain

[2] Univ Almeria, Fac Ciencias, Dept Quim Organ, Almeria 04120, Spain

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

关键词：

ABSOLUTE-CONFIGURATION; CYCLIZATION;

D O I：

10.1021/ol101173w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective total synthesis of liphagal, a selective inhibitor of PI3K alpha isolated from the marine sponge Aka coralliphaga, has been achieved. The novel tetracyclic "liphagane" skeleton is formed in one step, after the hydrogenation of a dihydroxydrimane phenol benzyl ether in the presence of cationic resin.

引用

页码：4450 / 4453

页数：4

共 24 条

[1] Synthesis of terpenoid unsaturated 1,4-dialdehydes.: π-facial selectivity in the Diels-Alder reaction of the 1-vinyl-2-methylcyclohexene moiety of polycyclic systems with DMAD [J].

Abad, A ;

Agulló, C ;

Castelblanque, L ;

Cuñat, AC ;

Navarro, I ;

de Arellano, MCR .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4189-4192

[2] Alternative syntheses of versatile chiral intermediate for drimane sesquiterpenes and labdane diterpenes using (R,R)-cycloheptane-1,2-diol as a chiral auxiliary [J].

Akita, H ;

Amano, Y ;

Kato, K ;

Kinoshita, M .

TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :725-732

[3] A thermal 6π electrocyclization strategy towards taiwaniaquinoids. First enantiospecific synthesis of (-)-taiwaniaquinone G [J].

Alvarez-Manzaneda, Enrique ;

Chahboun, Rachid ;

Cabrera, Eduardo ;

Alvarez, Esteban ;

Haidour, Ali ;

Miguel Ramos, Jose ;

Alvarez-Manzaneda, Ramon ;

Hmamouchi, Mohammed ;

Es-Samti, Hakima .

CHEMICAL COMMUNICATIONS, 2009, (05) :592-594

[4] Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)-norsesterterpene diene ester and (-)-subersic acid [J].

Arima, Yuusuke ;

Kinoshita, Masako ;

Akita, Hiroyuki .

TETRAHEDRON-ASYMMETRY, 2007, 18 (14) :1701-1711

[5]

BANERO AF, 1998, TETRADHEDRON, V54, P5635

[6] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Munro, Murray H. G. ;

Northcote, Peter T. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2010, 27 (02) :165-237

[7]

DOMMGUE G, 1991, TETRAHEDRON LETT, V32, P1765

[8] Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal [J].

George, Jonathan H. ;

Baldwin, Jack E. ;

Adlington, Robert M. .

ORGANIC LETTERS, 2010, 12 (10) :2394-2397

[9] Bioactive metabolites from the Caribbean sponge Aka coralliphagum [J].

Grube, Achim ;

Assmann, Michael ;

Lichte, Ellen ;

Sasse, Florenz ;

Pawlik, Joseph R. ;

Koeck, Matthias .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (04) :504-509

[10] The first total synthesis and determination of the absolute configuration of chapecoderin A, B and C [J].

Hagiwara, H ;

Takeuchi, F ;

Nozawa, M ;

Hoshi, T ;

Suzuki, T .

TETRAHEDRON, 2004, 60 (09) :1983-1989

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