Total Synthesis of (-)-Acutumine

被引：70

作者：

Li, Fang ^{[1
]}

Tartakoff, Samuel S. ^{[1
]}

Castle, Steven L. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 19期

基金：

美国国家科学基金会;

关键词：

MENISPERMUM-DAURICUM DC; CULTURED ROOTS; CORE STRUCTURE; ENOL ETHERS; ACUTUMINE; ALKALOIDS; REARRANGEMENT;

D O I：

10.1021/ja9024403

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the tetracyclic alkaloid (-)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted cyclization of an amine onto an alpha,beta-unsaturated dimethyl ketal.

引用

页码：6674 / +

页数：3

共 22 条

[1] PHENOL OXIDATION AND BIOSYNTHESIS .17. INVESTIGATIONS ON BIOSYNTHESIS OF SINOMENINE [J].

BARTON, DHR ;

KIRBY, AJ ;

KIRBY, GW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (08) :929-&

[2] Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride.: Facile synthesis of β-keto enol ethers [J].

Clerici, A ;

Pastori, N ;

Porta, O .

TETRAHEDRON, 2001, 57 (01) :217-225

[3] Synthesis of (-)-(Z)-deoxypukalide [J].

Donohoe, Timothy J. ;

Ironmonger, Alan ;

Kershaw, Neil M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7314-7316

[4] Rate acceleration of anionic oxy-Cope rearrangements induced by an additional unsaturation [J].

Gentric, L ;

Hanna, I ;

Huboux, A ;

Zaghdoudi, R .

ORGANIC LETTERS, 2003, 5 (20) :3631-3634

[5]

GOTO KAKUJI, 1929, BULL CHEM SOC JAPAN, V4, P220, DOI 10.1246/bcsj.4.220

[6] Synthesis of the acutumine spirocycle via a radical-polar crossover reaction [J].

Li, Fang ;

Castle, Steven L. .

ORGANIC LETTERS, 2007, 9 (20) :4033-4036

[7] Cyclohexadienone ketals and quinols: Four building blocks potentially useful for enantioselective synthesis [J].

Magdziak, D ;

Meek, SJ ;

Pettus, TRR .

CHEMICAL REVIEWS, 2004, 104 (03) :1383-1429

[8] Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine [J].

Moreau, Robert J. ;

Sorensen, Erik J. .

TETRAHEDRON, 2007, 63 (28) :6446-6453

[9] Enantioselective addition of allylzinc reagent to alkynyl ketones [J].

Nakamura, M ;

Hirai, A ;

Sogi, M ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5846-5847

[10] Synthesis of Isohasubanan Alkaloids via Enantioselective Ketone Allylation and Discovery of an Unexpected Rearrangement [J].

Nielsen, Daniel K. ;

Nielsen, Laura L. ;

Jones, Spencer B. ;

Toll, Lawrence ;

Asplund, Matthew C. ;

Castle, Steven L. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1187-1199

← 1 2 3 →