A new asymmetric synthesis of (+)-12b-epidevinylantirhine

被引：20

作者：

Allin, Steven M. ^{[1
]}

Khera, Jagjit S.

Witherington, Jason

Elsegood, Mark R. J.

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] GlaxoSmithKline Res Ltd, Dept Med Chem, Harlow CM19 5AW, Essex, England

[3] GlaxoSmithKline Res Ltd, Neurol & GI Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 32期

关键词：

D O I：

10.1016/j.tetlet.2006.06.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new asymmetric synthesis of the indole alkaloid derivative (+)-12b-epidevinylantirhine through stereoselective cyclization of a tethered indole nucleus onto an N-acyliminium ion intermediate, generated from a readily available non-racemic bicyclic lactam building block, and subsequent template modification through a highly diastereoselective conjugate addition protocol. In addition, we present the first X-ray crystal structure of this indole target. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5737 / 5739

页数：3

共 15 条

[1] Complementary stereoselective conjugate addition reactions on indolo[2,3-α]-quinolizine templates [J].

Allin, SM ;

Khera, JS ;

Thomas, CI ;

Witherington, J ;

Doyle, K ;

Elsegood, MRJ ;

Edgar, M .

TETRAHEDRON LETTERS, 2006, 47 (12) :1961-1964

[2] A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Doyle, K ;

Elsegood, MRJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4179-4186

[3] An asymmetric synthesis of both enantiomers of the indole alkaloid deplancheine [J].

Allin, SM ;

Thomas, CI ;

Doyle, K ;

Elsegood, MRJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :357-359

[4] Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Doyle, K ;

Elsegood, MRJ .

TETRAHEDRON LETTERS, 2004, 45 (38) :7103-7105

[5] Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates [J].

Amat, M ;

Pérez, M ;

Llor, N ;

Bosch, J .

ORGANIC LETTERS, 2002, 4 (16) :2787-2790

[6] Biogenetically inspired enantioselective approach to indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin [J].

Bassas, O ;

Llor, N ;

Santos, MMM ;

Griera, R ;

Molins, E ;

Amat, M ;

Bosch, J .

ORGANIC LETTERS, 2005, 7 (14) :2817-2820

[7] Biomimetic entry to the sarpagan family of indole alkaloids:: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine [J].

Deiters, A ;

Chen, K ;

Eary, CT ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) :4541-4550

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

Deiters, A ;

Martin, SF .

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

[9] A new entry to the isogeissoschizoid skeleton [J].

Fornicola, RS ;

Subburaj, K ;

Montgomery, J .

ORGANIC LETTERS, 2002, 4 (04) :615-617

[10] Radical cyclisation with high diastereofacial selectivity: Asymmetric synthesis of (+)-12b-epidevinylantirhine [J].

Ihara, M ;

Katsumata, A ;

Fukumoto, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (07) :991-992

← 1 2 →