Enantioselective Allylation of β-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin

被引：15

作者：

Koukal, Petr ^{[1
]}

Ulc, Jan ^{[1
]}

Necas, David ^{[1
]}

Kotora, Martin ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Hlavova 8, Prague 12343 2, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 12期

关键词：

Asymmetric synthesis; Allylation; Aldehydes; BrOnsted acids; Lewis bases; ICHTHYOTOXIC CYCLIC LIPOPEPTIDE; ACID-CATALYZED ALLYLBORATION; RING-CLOSING METATHESIS; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; PAPULACANDIN-B; BIPYRIDINE N; N'-DIOXIDES; ANTIFUNGAL ACTIVITY; ALLYLIC ALCOHOLS; ANTIBIOTICS;

D O I：

10.1002/ejoc.201600286

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comparative study of the catalytic allylations and crotylations of (E)-and (Z)-haloacrylaldehydes by Lewis bases (chiral N,N'-dioxides) and Bronsted acids (chiral phosphoric acids) was undertaken. The reactions proceeded with high enantio- and diastereoselectivities with slightly better asymmetric induction observed in the case of N,N'-dioxide catalysis. The formed enantioenriched chiral unsaturated haloalcohols could be considered general building blocks, as they could be used in the syntheses of more complex natural products possessing substituted 1,3-diene fragments. This was exemplified by the formal total syntheses of pteronenone and antillatoxin.

引用

页码：2110 / 2114

页数：5

共 66 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] Synthesis of a promising immunosuppressant: FR252921 [J].

Amans, Dominique ;

Bellosta, Veronique ;

Cossy, Janine .

ORGANIC LETTERS, 2007, 9 (23) :4761-4764

[3] γ-Silylboronates in the chiral Bronsted acid-catalysed allylboration of aldehydes [J].

Barrio, P. ;

Rodriguez, E. ;

Saito, K. ;

Fustero, S. ;

Akiyama, T. .

CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5246-5249

[4]

Bassetti M, 2013, CURR ORG CHEM, V17, P2654

[5] Stereoselective reactions involving hypervalent silicate complexes [J].

Benaglia, Maurizio ;

Guizzetti, Stefania ;

Pignataro, Luca .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :492-512

[6] Natural (5′-oxoheptene-1′E,3′E-dienyl)-5,6-dihydro-2H-pyran-2-one:: total synthesis and revision of its absolute configuration [J].

Bouzbouz, S ;

de Lemos, E ;

Cossy, J ;

Saez, J ;

Franck, X ;

Figadère, B .

TETRAHEDRON LETTERS, 2004, 45 (12) :2615-2617

[7] Enantioselective Allylation of tert-Butyldimethylsilyl-Protected Vanillin and Synthesis of a Lignan Derivative Isolated from Machilus wangchiana [J].

Cadart, Timothee ;

Koukal, Petr ;

Kotora, Martin .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (34) :7556-7560

[8] Total synthesis of papulacandin D [J].

Denmark, Scott E. ;

Regens, Christopher S. ;

Kobayashi, Tetsuya .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) :2774-+

[9] Total synthesis of (+)-papulacandin D [J].

Denmark, Scott E. ;

Kobayashi, Tetsuya ;

Regens, Christopher S. .

TETRAHEDRON, 2010, 66 (26) :4745-4759

[10] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

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