ortho-Quinone Methides in Natural Product Synthesis

被引：348

作者：

Willis, Nicky J. ^{[1
]}

Bray, Christopher D. ^{[1
]}

机构：

[1] Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 30期

基金：

英国工程与自然科学研究理事会;

关键词：

benzopyran; cycloaddition; electrocyclic reactions; natural products; ortho-quinone methide; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; BIOMIMETIC SYNTHESIS; FORMAL SYNTHESIS; CONCISE SYNTHESIS; BERKELIC ACID; ROBUSTADIAL-A; GENERATION; CYCLIZATION;

D O I：

10.1002/chem.201200619

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

ortho-Quinone methides (o-QMs) are emerging as highly useful intermediates, the inherent reactivity of which can be used in linchpin reactions for the construction of complex natural products. This review encompasses the major contributions in this field, exemplifying the major strategies and reactivity modes which can be applied.

引用

页码：9160 / 9173

页数：14

共 97 条

[1] A biomimetic synthesis of lucidene [J].

Adlington, RM ;

Baldwin, JE ;

Pritchard, GJ ;

Williams, AJ ;

Watkin, DJ .

ORGANIC LETTERS, 1999, 1 (12) :1937-1939

[2] Taming reactive phenol tautomers and o-quinone methides with transition metals:: A structure-reactivity relationship [J].

Amouri, H ;

Le Bras, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (07) :501-510

[3] General synthesis, first crystal structure, and reactivity of stable o-quinone methide complexes of Cp*Ir [J].

Amouri, H ;

Besace, Y ;

Le Bras, J ;

Vaissermann, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :6171-6172

[4] Total Syntheses of ent-Heliespirones A and C [J].

Bai, Wen-Ju ;

Green, Jason C. ;

Pettus, Thomas R. R. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :379-387

[5] Generation of ortho-Quinone Methides by p-TsOH on Silica and Their Hetero-Diels-Alder Reactions with Styrenes [J].

Batsomboon, Paratchata ;

Phakhodee, Wong ;

Ruchirawat, Somsak ;

Ploypradith, Poonsakdi .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :4009-4012

[6] A Concise Synthesis of Berkelic Acid Inspired by Combining the Natural Products Spicifernin and Pulvilloric Acid [J].

Bender, Christopher F. ;

Yoshimoto, Francis K. ;

Paradise, Christopher L. ;

De Brabander, Jef K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) :11350-+

[7] A two-step biomimetic synthesis of antimalarial robustadials A and B [J].

Bharate, Sandip B. ;

Singh, Inder Pal .

TETRAHEDRON LETTERS, 2006, 47 (39) :7021-7024

[8] Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide [J].

Bishop, Lee M. ;

Winkler, Michael ;

Houk, Kendall N. ;

Bergman, Robert G. ;

Trauner, Dirk .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) :5405-5408

[9] ONE-POT SYNTHESIS OF PRECOCENE-I AND PRECOCENE-II AND A FORMAL SYNTHESIS OF ROBUSTADIAL-A AND ROBUSTADIAL-B VIA 2-PHENYL-4H-1,3,2-BENZODIOXABORIN [J].

BISSADA, S ;

LAU, CK ;

BERNSTEIN, MA ;

DUFRESNE, C .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (08) :1866-1869

[10] On the dimers of β-tocopherol [J].

Boehmdorfer, Stefan ;

Patel, Anjan ;

Netscher, Thomas ;

Gille, Lars ;

Rosenau, Thomas .

TETRAHEDRON, 2011, 67 (26) :4858-4861

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