The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

被引：89

作者：

Bradshaw, Ben ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Lab Quim Organ, IBUB, E-08028 Barcelona, Spain

来源：

SYNLETT | 2012年 / 03期

关键词：

Wieland-Miescher ketone; enantioselective direct aldol reaction; asymmetric organocatalysis; total synthesis; natural products; STEREOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC ROBINSON ANNULATION; ONE-POT; SELECTIVE REDUCTION; CONJUGATE ADDITION; CARBONYL-COMPOUNDS; INDOLE DITERPENE; ABSOLUTE-CONFIGURATION; ISOXAZOLE ANNELATION;

D O I：

10.1055/s-0031-1290107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Hajos-Parrish-Eder-Sauer-Wiechert reaction can be considered as the origin of asymmetric organocatalysis, giving rise to the Wieland-Miescher ketone 1 (WMK), a versatile building block. Although 40 years have passed since its discovery, a highly enantioselective and scalable synthesis of the WMK has remained elusive. This account details a solution to that problem that came about in the development of methodology towards C-8a WMK analogues as part of the total synthesis of complex diterpene natural products. The work has been placed in the context of the historical background and reactivity of this important building block, highlighting the challenges faced by organocatalysis in large-scale reactions.

引用

页码：337 / 356

页数：20

共 200 条

[61]

GEETHA P, 1979, TETRAHEDRON LETT, P565

[62] ANTIINSECTAN AFLAVININE DERIVATIVES FROM THE SCLEROTIA OF ASPERGILLUS-FLAVUS [J].

GLOER, JB ;

TEPASKE, MR ;

SIMA, JS ;

WICKLOW, DT ;

DOWD, PF .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5457-5460

[63] NOMININE - A NEW INSECTICIDAL INDOLE DITERPENE FROM THE SCLEROTIA OF ASPERGILLUS-NOMIUS [J].

GLOER, JB ;

RINDERKNECHT, BL ;

WICKLOW, DT ;

DOWD, PF .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2530-2532

[64] AN ENANTIOSELECTIVE APPROACH TO RING A OF TAXOL USING THE WIELAND-MIESCHER KETONE [J].

GOLINSKI, M ;

VASUDEVAN, S ;

FLORESCA, R ;

BROCK, CP ;

WATT, DS .

TETRAHEDRON LETTERS, 1993, 34 (01) :55-58

[65] ADDITION OF TERT-BUTYLDIMETHYLSILYL OR TERT-BUTYLDIPHENYLSILYL CYANIDE TO HINDERED KETONES [J].

GOLINSKI, M ;

BROCK, CP ;

WATT, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :159-164

[66]

GOPALAKRISHNAN G, 1983, SYNTHESIS-STUTTGART, P797

[67] SELECTIVE RING EXPANSION OF DELTA5,10-OCTALIN-1,6-DIONES VIA SCHMIDT REACTION [J].

GRECO, CV ;

GRAY, RP .

TETRAHEDRON, 1970, 26 (18) :4329-&

[68] SYNTHETIC STUDIES ON QUASSINOIDS - TOTAL SYNTHESIS OF (-)-CHAPARRINONE, (-)-GLAUCARUBOLONE, AND (+)-GLAUCARUBINONE [J].

GRIECO, PA ;

COLLINS, JL ;

MOHER, ED ;

FLECK, TJ ;

GROSS, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6078-6093

[69] KINETIC ENOLATES OF ENEDIONE SYSTEMS RELATED TO THE WIELAND-MIESCHER KETONE [J].

GRIECO, PA ;

FERRINO, S ;

OGURI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2593-2594

[70] A NEW RING EXPANSION APPROACH TO 3-FORMYL-2-CYCLOHEPTEN-1-ONES [J].

GUERRERO, A ;

PARRILLA, A ;

CAMPS, F .

TETRAHEDRON LETTERS, 1990, 31 (13) :1873-1876

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