Concise formal synthesis of (-)-peduncularine via ring-closing metathesis

被引：53

作者：

Washburn, DG ^{[1
]}

Heidebrecht, RW ^{[1
]}

Martin, SF ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 19期

关键词：

D O I：

10.1021/ol0354066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A synthesis of the 6-aza[3.2.1]bicyclooctene (-)-2 has been completed by a short sequence of reactions that required only six operations from (S)-malic acid and featured a novel ring-closing metathesis to form the bridged bicyclic ring. Because 2 was previously converted into (-)- peduncularine (1), its preparation constitutes a formal enantioselective synthesis of 1.

引用

页码：3523 / 3525

页数：3

共 25 条

[1] Ruthenium carbene complexes with imidazol-2-ylidene ligands:: Syntheses of conduritol derivatives reveals superior RCM activity [J].

Ackermann, L ;

El Tom, D ;

Fürstner, A .

TETRAHEDRON, 2000, 56 (15) :2195-2202

[2] PEDUNCULARINE, AN INDOLE-PYRROLIZIDINE ALKALOID [J].

BICK, IRC ;

BREMNER, JB ;

PRESTON, NW .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (19) :1155-&

[3]

BICK IRC, 1985, ALKALOIDS, V24, P113

[4] SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE [J].

BROWN, DS ;

CHARREAU, P ;

HANSSON, T ;

LEY, SV .

TETRAHEDRON, 1991, 47 (07) :1311-1328

[5] Stereoselective total synthesis of dihydrocorynantheol [J].

Deiters, A ;

Martin, SF .

ORGANIC LETTERS, 2002, 4 (19) :3243-3245

[6] Application of ring-closing metathesis to the formal total synthesis of (+)-FR900482 [J].

Fellows, IM ;

Kaelin, DE ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :10781-10787

[7]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[8] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[9] Enantioselective total syntheses of manzamine A and related alkaloids [J].

Humphrey, JM ;

Liao, YS ;

Ali, A ;

Rein, T ;

Wong, YL ;

Chen, HJ ;

Courtney, AK ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) :8584-8592

[10] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ARISTOTELIA ALKALOID PEDUNCULARINE [J].

KLAVER, WJ ;

HIEMSTRA, H ;

SPECKAMP, WN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2588-2595

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