Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4+2]-Annulation Reaction

被引：44

作者：

Danda, Adithi ^{[1
,2
]}

Kesava-Reddy, Naredla ^{[1
]}

Golz, Christopher ^{[2
]}

Strohmann, Carsten ^{[2
]}

Kumar, Kamal ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 11期

关键词：

DIELS-ALDER REACTION; 1,3-BIS-SILYL ENOL ETHERS; N-ACYL AMINOPHOSPHINES; 4+2 ANNULATION; NATURAL-PRODUCTS; DOMINO REACTIONS; DRUG DISCOVERY; ALLENOATES; CHROMONE; CYCLOADDITIONS;

D O I：

10.1021/acs.orglett.6b01030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic addition of the amino acid derived bifunctional N-acylaminophosphine to an alpha-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis Anther paves the way to two different classes of complex, sp(3)-rich tetracyclic benzopyrans via efficient cascade reactions.

引用

页码：2632 / 2635

页数：4

共 53 条

[31] Chiral Tertiary Amine Thiourea-Catalyzed Asymmetric Inverse-Electron-Demand Die Is Alder Reaction of Chromone Heterodienes Using 3-Vinylindoles as Dienophiles [J].

Mao, Zhijie ;

Lin, Aijun ;

Shi, Yan ;

Mao, Haibin ;

Li, Weipeng ;

Cheng, Yixiang ;

Zhu, Chengjian .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10233-10239

[32] Nucleophilic phosphine organocatalysis [J].

Methot, JL ;

Roush, WR .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1035-1050

[33] Total syntheses and structural revision of α and β-diversonolic esters and total syntheses of diversonol and blennolide C [J].

Nicolaou, K. C. ;

Li, Ang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6579-6582

[34] Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans [J].

Nicolaou, KC ;

Pfefferkorn, JA ;

Roecker, AJ ;

Cao, GQ ;

Barluenga, S ;

Mitchell, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :9939-9953

[35] The total synthesis of the fungal metabolite diversonol [J].

Nising, CF ;

Ohnemüller, UK ;

Bräse, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (02) :307-309

[36] Vinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products [J].

Qin, Tian ;

Johnson, Richard P. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1714-1717

[37]

Sabitha G., 1996, ALDRICHIM ACTA, P29

[38] Application of the Suzuki-Miyaura Reaction in the Synthesis of Flavonoids [J].

Selepe, Mamoalosi A. ;

Van Heerden, Fanie R. .

MOLECULES, 2013, 18 (04) :4739-4765

[39] On the stereochemistry of the dihydropyrone Diels-Alder reaction [J].

Seth, PP ;

Totah, NI .

ORGANIC LETTERS, 1999, 1 (09) :1411-1414

[40] Studies toward the synthesis of phomactin A. An approach to the macrocyclic core [J].

Teng, Dawei ;

Wang, Bo ;

Augatis, Alex J. ;

Totah, Nancy I. .

TETRAHEDRON LETTERS, 2007, 48 (26) :4605-4607

← 1 2 3 4 5 6 →