Use of a Tandem Prins/Friedel-Crafts Reaction in the Construction of the Indeno-Tetrahydropyridine Core of the Haouamine Alkaloids: Formal Synthesis of (-)-Haouamine A

被引：50

作者：

Fenster, Erik ^{[1
]}

Fehl, Charlie ^{[1
]}

Aube, Jeffrey ^{[1
]}

机构：

[1] Univ Kansas, KU Chem Methodol & Lib Dev Ctr, Lawrence, KS 66047 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

3-COMPONENT SYNTHESIS; ONE-POT; CYCLIZATION;

D O I：

10.1021/ol200725m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem Prins/friedel-Crafts reaction useful for the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids and a formal synthesis of (-)-haouamine A are described.

引用

页码：2614 / 2617

页数：4

共 21 条

[11] One-Pot, Three-Component Synthesis of 4-Aryl-5,6-dihydropyran via Prins-Friedel-Crafts Reaction [J].

Reddy, Udagandla C. ;

Saikia, Anil K. .

SYNLETT, 2010, (07) :1027-1032

[12] Development and applications of amino acid derived organometallics [J].

Rilatt, I ;

Caggiano, L ;

Jackson, RFW .

SYNLETT, 2005, (18) :2701-2719

[13] Much Improved Conditions for the Negishi Cross-Coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides [J].

Ross, Andrew J. ;

Lang, Hannah L. ;

Jackson, Richard F. W. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :245-248

[14] Facile synthesis of the indeno-tetrahydropyridine core of haouamine A [J].

Smith, ND ;

Hayashida, J ;

Rawal, VH .

ORGANIC LETTERS, 2005, 7 (20) :4309-4312

[15] Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B [J].

Tanaka, Takeshi ;

Inui, Hiromi ;

Kida, Hiroshi ;

Kodama, Takeshi ;

Okamoto, Takuya ;

Takeshima, Aki ;

Tachi, Yoshimitsu ;

Morimoto, Yoshiki .

CHEMICAL COMMUNICATIONS, 2011, 47 (10) :2949-2951

[16] Formal Total Synthesis of Haouamine A [J].

Taniguchi, Tsuyoshi ;

Zaimoku, Hisaaki ;

Ishibashi, Hiroyuki .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2624-2626

[17] Synthesis and structure revision of calyxin natural products [J].

Tian, X ;

Jaber, JJ ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) :3176-3183

[18] Chemoselectivity of the ruthenium-catalyzed hydrative diyne cyclization: Total synthesis of (+)-cylindricine C, D, and E [J].

Trost, BM ;

Rudd, MT .

ORGANIC LETTERS, 2003, 5 (24) :4599-4602

[19]

WILLIAMS JM, 1995, TETRAHEDRON LETT, V36, P5461

[20] Synthesis of the 3-Aza-[7]-paracyclophane core of Haouamine A and B [J].

Wipf, P ;

Furegati, M .

ORGANIC LETTERS, 2006, 8 (09) :1901-1904

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