Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B

被引：10

作者：

Tanaka, Takeshi ^{[1
]}

Inui, Hiromi ^{[1
]}

Kida, Hiroshi ^{[1
]}

Kodama, Takeshi ^{[1
]}

Okamoto, Takuya ^{[1
]}

Takeshima, Aki ^{[1
]}

Tachi, Yoshimitsu ^{[1
]}

Morimoto, Yoshiki ^{[1
]}

机构：

[1] Osaka City Univ, Dept Chem, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 10期

基金：

日本学术振兴会;

关键词：

FORMAL TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALKALOIDS; ROUTE; SALTS;

D O I：

10.1039/c0cc04453a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The characteristic indeno-tetrahydropyridine core of cytotoxic haouamine B (2) was efficiently synthesized featuring the diastereoselective construction of a diaryl-substituted stereogenic quaternary center by an intramolecular Pd-catalyzed alpha-C-arylation and subsequent direct conversion of the vinylogous imide function into the C2-C25 double bond by TsNHNH(2).

引用

页码：2949 / 2951

页数：3

共 25 条

[1] THE RELATIVE STABILITIES OF CIS-TRANS ISOMERS OF FUSED RING SYSTEMS CONTAINING ANGULAR METHYL GROUPS [J].

BACHMANN, WE ;

ROSS, A ;

DREIDING, AS ;

SMITH, PAS .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (02) :222-240

[2] Total synthesis of (±)-haouamine A [J].

Baran, PS ;

Burns, NZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3908-3909

[3] Calculated chemical shifts as a fine tool of conformational analysis: An unambiguous solution for haouamine alkaloids [J].

Belostotskii, Anatoly M. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :5723-5731

[4] On the origin of the haouamine alkaloids [J].

Burns, Noah Z. ;

Baran, Phil S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :205-208

[5] Total synthesis of haouamine A: the indeno-tetrahydropyridine core [J].

Burns, Noah Z. ;

Jessing, Mikkel ;

Baran, Phil S. .

TETRAHEDRON, 2009, 65 (33) :6600-6610

[6] Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer [J].

Burns, Noah Z. ;

Krylova, Irina N. ;

Hannoush, Rami N. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) :9172-+

[7] Suzuki-type cross-coupling reaction of 3-iodoindazoles with aryl boronic acids: a general and flexible route to 3-arylindazoles [J].

Collot, V ;

Dallemagne, P ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 1999, 55 (22) :6917-6922

[8] Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones [J].

Comins, DL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) :1491-1500

[9] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

JOSEPH, SP ;

GOEHRING, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4719-4728

[10] REGIOSPECIFIC SUBSTITUTION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES AT C-5 VIA HALOGENATION AND CROSS-COUPLING [J].

COMINS, DL ;

JOSEPH, SP ;

CHEN, XH .

TETRAHEDRON LETTERS, 1995, 36 (50) :9141-9144

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