Abstract
AbstractThe preparation and utilization of specific biaryl systems, particularly those which suffer hindered rotation, is a demanding goal not only in the synthesis of natural products and Pharmaceuticals, but also for example in the discovery of new reagents for asymmetric synthesis. This article will attempt to provide a topical review of modern, efficient processes for the specific preparation of biaryls. This appears to be of particular urgency, since, under the pressure of continually increasing demand, a wealth of new or modified synthetic approaches to the ever more important biaryl systems has been realized in recent years. The high standard which has been reached in this field is impressively demonstrated by regio‐ and stereoselective syntheses of important biaryl natural products such as steganone, ancistrocladine, ancistrocladisine, and dioncophylline A. Besides the utilization of asymmetric induction in the actual coupling step, the thermodynamically or kinetically controlled torsion of biaryl axes belongs to the most important concepts discussed.
References
190
Referenced
558
{'key': 'e_1_2_1_1_2', 'volume-title': 'Natural Product Chemistry', 'author': 'Torssell K. G. B.', 'year': '1983'}
/ Natural Product Chemistry by Torssell K. G. B. (1983){'key': 'e_1_2_1_1_3', 'volume-title': 'Biosynthesis of Natural Products', 'author': 'Manitto P.', 'year': '1981'}
/ Biosynthesis of Natural Products by Manitto P. (1981){'key': 'e_1_2_1_1_4', 'volume-title': 'The Chemistry of Natural Products', 'author': 'Thomson R. H.', 'year': '1985'}
/ The Chemistry of Natural Products by Thomson R. H. (1985){'key': 'e_1_2_1_1_5', 'volume-title': 'Introduction to Alkaloids, A Biogenetic Approach', 'author': 'Cordell G. A.', 'year': '1981'}
/ Introduction to Alkaloids, A Biogenetic Approach by Cordell G. A. (1981){'key': 'e_1_2_1_2_2', 'first-page': '1413', 'volume': '1974', 'author': 'Govindachari T.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Govindachari T.10.1016/S0099-9598(08)60248-5
10.1135/cccc19882664
10.1021/jo00208a051
10.1021/jo00233a024
10.1021/ja00785a054
10.1016/0040-4039(80)88012-9
10.1126/science.183.4127.803
10.1021/ja00334a041
10.1039/cs9891800187
10.1002/ange.19881000804
10.1002/anie.198810093
10.1016/0263-7855(89)80053-0
10.1016/S0021-9673(00)81004-3
10.1002/ange.19891010411
10.1002/anie.198904861
10.1021/ja00330a039
10.1016/S0040-4039(00)82046-8
{'key': 'e_1_2_1_17_3', 'first-page': '18', 'volume': '1977', 'author': 'Yamamuro K.', 'journal-title': 'Synlett'}
/ Synlett by Yamamuro K.10.1002/nadc.19880361207
10.1016/S0040-4020(01)85938-X
10.1021/cr00078a005
10.1016/0040-4020(80)80185-2
10.1021/jo00885a034
10.1002/cber.190103402141
10.1055/s-1974-23219
/ Synthesis by Fanta P. E.10.1016/0040-4020(82)85093-X
{'key': 'e_1_2_1_25_2', 'first-page': '383', 'volume': '1977', 'author': 'Gauthier S.', 'journal-title': 'Synthesis'}
/ Synthesis by Gauthier S.10.1002/jhet.5570240204
10.1016/0041-624X(87)90011-4
{'key': 'e_1_2_1_27_3', 'first-page': '96106r', 'volume': '107', 'year': '1987', 'journal-title': 'C. A.'}
/ C. A. (1987)10.1246/bcsj.55.1144
- For exceptions see e.g. [24];
{'key': 'e_1_2_1_29_3', 'first-page': '329', 'volume': '108', 'author': 'Dallacker F.', 'year': '1984', 'journal-title': 'Chem.‐Ztg.'}
/ Chem.‐Ztg. by Dallacker F. (1984)10.1071/CH9881087
10.1021/ja00411a034
10.1021/ic50203a050
10.1021/jo00154a018
10.1139/v89-164
10.1016/0022-328X(86)80118-8
10.1021/om00100a019
10.1246/bcsj.57.1887
10.1021/jo00364a002
10.1016/0022-328X(84)85152-9
{'key': 'e_1_2_1_40_2', 'volume-title': 'Oxidative Coupling of Phenols', 'author': 'Taylor W. I.', 'year': '1967'}
/ Oxidative Coupling of Phenols by Taylor W. I. (1967){'key': 'e_1_2_1_41_2', 'volume-title': 'Festschrift Prof. A. Stoll zum siebzigsten Geburtstag', 'author': 'Barton D. H. R.', 'year': '1957'}
/ Festschrift Prof. A. Stoll zum siebzigsten Geburtstag by Barton D. H. R. (1957){'key': 'e_1_2_1_42_2', 'first-page': '2345', 'volume': '1977', 'author': 'Young D. A.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Young D. A.10.1016/S0040-4039(00)81607-X
10.1002/hlca.19890720221
10.1021/jo00328a029
10.1021/jo00274a007
10.1021/jo01292a051
10.1021/jo00335a045
{'key': 'e_1_2_1_47_2', 'first-page': '2420', 'volume': '1977', 'author': 'Laatsch H.', 'journal-title': 'Liebigs Ann. Chem.'}
/ Liebigs Ann. Chem. by Laatsch H.10.1021/jo00245a035
10.1021/jo00206a003
{'key': 'e_1_2_1_49_2', 'first-page': '1305', 'volume': '1988', 'author': 'Hewgill F. R.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Hewgill F. R.10.1002/ange.19881001217
10.1002/anie.198817051
10.1021/ja00541a020
10.1016/B978-0-12-697253-5.50008-0
10.5059/yukigoseikyokaishi.46.192
10.1055/s-1972-21967
10.1002/ange.19790910604
10.1002/anie.197904291
10.1002/ange.19670791712
{'key': 'e_1_2_1_56_3', 'first-page': '799', 'volume': '6', 'year': '1967', 'journal-title': 'Angew. Chem. Int. Ed. Engl.'}
/ Angew. Chem. Int. Ed. Engl. (1967)10.1021/jo00335a079
10.1071/CH9842119
{'key': 'e_1_2_1_59_2', 'first-page': '308', 'volume': '27', 'author': 'Gunasekaran A.', 'year': '1988', 'journal-title': 'Ind. J. Chem. Sect.'}
/ Ind. J. Chem. Sect. by Gunasekaran A. (1988)10.3987/S-1981-02-0709
10.1021/jo00327a026
10.1021/ja00541a021
10.1016/S0040-4039(00)80622-X
10.1021/ja00303a027
{'key': 'e_1_2_1_65_2', 'first-page': '1179', 'volume': '1977', 'author': 'Magnus P.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Magnus P.10.1080/00397918008062764
10.1021/jo00191a037
10.1071/CH9841775
10.1016/S0040-4039(00)95617-X
10.1016/S0040-4039(00)95777-0
10.1248/cpb.34.3159
10.1248/cpb.33.3599
{'key': 'e_1_2_1_72_2', 'first-page': '1195', 'volume': '1977', 'author': 'Majeed A. J.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Majeed A. J.{'key': 'e_1_2_1_72_3', 'first-page': '2053', 'volume': '1977', 'author': 'Bird P.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Bird P.10.1016/0040-4020(80)85040-X
{'key': 'e_1_2_1_74_2', 'first-page': '1511', 'volume': '1981', 'author': 'Nishiyama S.', 'journal-title': 'Chem. Lett.'}
/ Chem. Lett. by Nishiyama S.{'key': 'e_1_2_1_75_2', 'first-page': '2573', 'volume': '1984', 'author': 'Carvalho C. F.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Carvalho C. F.{'key': 'e_1_2_1_75_3', 'first-page': '1621', 'volume': '1984', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 110.1248/cpb.37.1744
10.1071/CH9842111
10.1016/S0040-4020(01)91149-4
{'key': 'e_1_2_1_79_2', 'volume-title': 'Palladium Reagents in Organic Syntheses', 'author': 'Heck R. F.', 'year': '1985'}
/ Palladium Reagents in Organic Syntheses by Heck R. F. (1985)10.1016/0040-4039(88)85066-4
10.1016/S0040-4039(01)81225-9
10.3987/R-1985-08-1943
10.3987/S-1987-01-0155
10.1021/jo01319a052
10.1021/jo00176a015
10.1016/S0040-4039(00)80145-8
10.1021/jo00281a028
10.1016/S0040-4039(00)94569-6
10.1021/ja00522a058
10.1248/cpb.23.2578
10.1021/ja01854a006
10.1016/B978-008046518-0.00121-5
10.1021/ar00083a001
10.1351/pac198052030669
{'key': 'e_1_2_1_93_2', 'first-page': '521', 'volume': '1977', 'author': 'Larson E. R.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Larson E. R.10.1016/S0040-4020(01)87628-6
{'key': 'e_1_2_1_95_2', 'first-page': '2299', 'volume': '1982', 'author': 'Cornforth J.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Cornforth J.{'key': 'e_1_2_1_95_3', 'first-page': '136', 'volume': '1985', 'author': 'Carter S. D.', 'journal-title': 'J. Chem. Res. (S)'}
/ J. Chem. Res. (S) by Carter S. D.10.1021/jo00254a012
10.1016/0022-328X(83)85077-3
10.1016/0022-328X(84)80165-5
10.1080/00397918108063618
10.1016/S0040-4039(00)94359-4
10.1002/ange.19860980605
{'key': 'e_1_2_1_100_3', 'first-page': '505', 'volume': '25', 'year': '1986', 'journal-title': 'Angew. Chem. Int. Ed. Engl.'}
/ Angew. Chem. Int. Ed. Engl. (1986)10.1016/S0040-4039(00)95599-0
10.1016/S0040-4039(00)95600-4
10.1002/ange.19891010722
10.1002/anie.198909291
10.1021/jo00200a045
10.1021/ja00511a032
10.1071/CH9881711
10.1016/S0040-4039(00)84964-3
10.1021/ja00252a029
{'key': 'e_1_2_1_108_2', 'first-page': '1711', 'volume': '1989', 'author': 'Hatanaka Y.', 'journal-title': 'Chem. Lett.'}
/ Chem. Lett. by Hatanaka Y.10.1021/ja00858a034
10.1021/jo00401a018
10.1021/ja00367a053
10.1021/ja00289a023
10.1071/CH9900079
{'key': 'e_1_2_1_113_2', 'first-page': '301', 'volume': '1989', 'author': 'Rizzacasa M. A.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Rizzacasa M. A.{'key': 'e_1_2_1_114_2', 'first-page': '1787', 'volume': '1989', 'author': 'Hughes A. B.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Hughes A. B.{'key': 'e_1_2_1_115_2', 'first-page': '2425', 'volume': '1988', 'author': 'Rizzacasa M. A.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Rizzacasa M. A.10.1016/S0040-4039(00)81338-6
10.1021/jo00240a012
10.1139/v87-072
10.1016/S0040-4039(00)94588-X
10.1071/CH9880305
{'key': 'e_1_2_1_121_2', 'volume-title': 'Circular Dichroic Spectroscopy – Exciton Coupling in Organic Stereochemistry', 'author': 'Harada N.', 'year': '1983'}
/ Circular Dichroic Spectroscopy – Exciton Coupling in Organic Stereochemistry by Harada N. (1983){'key': 'e_1_2_1_122_2', 'first-page': '590', 'volume': '22', 'author': 'Parthasarathy P. C.', 'year': '1983', 'journal-title': 'Ind. J. Chem. Sect.'}
/ Ind. J. Chem. Sect. by Parthasarathy P. C. (1983)10.1021/np50040a003
{'key': 'e_1_2_1_124_2', 'first-page': '181', 'volume-title': "The Stereocontrolled Total Synthesis of Naphthyl Isoquinoline Alkaloids: Symposia in print of the “6ème Colloque International, consacré aux Plantes Médicinales et Substances d'Origine Naturelle”", 'author': 'Bringmann G.', 'year': '1988'}
/ The Stereocontrolled Total Synthesis of Naphthyl Isoquinoline Alkaloids: Symposia in print of the “6ème Colloque International, consacré aux Plantes Médicinales et Substances d'Origine Naturelle” by Bringmann G. (1988)- In the case of very electron‐poor aromatic compounds (such as oxazoline‐substituted quinolines) the electrophilic coupling partner does not require a nucleofugal group;
10.1021/ja00316a063
10.1021/ja00252a022
10.1021/jo00199a036
10.1021/ja00367a054
10.1016/S0040-4020(01)96682-7
{'key': 'e_1_2_1_130_2', 'first-page': '1490', 'volume': '1954', 'author': 'Yamamoto K.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Yamamoto K.{'key': 'e_1_2_1_131_2', 'first-page': '168', 'volume': '1957', 'author': 'Yamamoto K.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Yamamoto K.10.1021/ja00232a030
10.1016/S0040-4039(00)99427-9
10.1016/S0040-4039(00)95163-3
10.1071/CH9880897
10.1071/CH9880919
10.1016/S0040-4039(00)84374-9
10.1021/jo00236a056
10.1016/S0040-4020(01)82416-9
- In another example an unnatural but biologically more active aza‐analogous dibenzocyclooctadiene the thermodynamic equilibrium even lies at only 1:40;
10.1016/S0040-4039(00)99166-4
10.1248/cpb.33.121
{'key': 'e_1_2_1_142_2', 'first-page': '1233', 'volume': '1977', 'author': 'Miyano S.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Miyano S.10.1246/bcsj.58.1345
10.1246/bcsj.59.235
10.1246/bcsj.61.3249
10.1246/bcsj.57.1943
10.1246/bcsj.54.3522
10.1016/S0040-4039(01)93754-2
10.1002/ange.19860981019
10.1002/anie.198609131
10.3987/COM-88-S62
10.1016/S0040-4039(00)94589-1
-
(a)G.Bringmann F.Pokorny H.Reuscher D.Lisch L.Aké Assi Planta med.56(1990) in press;
(
10.1055/s-2006-961026
) - (b)G.Bringmann D.Lisch H.Renscher L.Aké Assi K.Günther Phytochemistry in press.
- A further advantage of this process is that apart from42and43hydroxymethyl compounds of type41and lactones of type40are found as natural products in the same plants and can thus be included synthetically without additional effort:G.Bringmann M.Rübenacker J. R.Jansen T.Gender L.Aké Assi Planta med.56(1990) in press.
- In contrast precomplexation of the alkali metal cation ofbasichydride transfer reagents at nitrogen and attack of the anionic hydride part of the reagent from the same side (i.e. from above) should lead to the other lactolate diastercomer (not shown in Scheme 27) which bears the hydrogen in β‐position; this isomer should react in an analogous manner to give45b.
10.1002/ange.19891011227
10.1002/anie.198916721
- See for example the non‐stereoselective synthesis of a (probably not separable) mixture of all four possible stereoisomeric ancistrocladisines [113].
- G.Bringmann M.Berndsen R.Walter unpublished.
- G.Bringmann C.Ewers unpublished.
- G.Bringmann T.Hartung unpublished.
Dates
Type | When |
---|---|
Created | 21 years, 8 months ago (Dec. 30, 2003, 7:09 p.m.) |
Deposited | 1 year, 10 months ago (Oct. 10, 2023, 9:05 a.m.) |
Indexed | 1 month, 1 week ago (July 27, 2025, 3:16 a.m.) |
Issued | 35 years ago (Sept. 1, 1990) |
Published | 35 years ago (Sept. 1, 1990) |
Published Online | 21 years, 8 months ago (Dec. 22, 2003) |
Published Print | 35 years ago (Sept. 1, 1990) |
@article{Bringmann_1990, title={The Directed Synthesis of Biaryl Compounds: Modern Concepts and Strategies}, volume={29}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199009771}, DOI={10.1002/anie.199009771}, number={9}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Bringmann, Gerhard and Walter, Rainer and Weirich, Ralf}, year={1990}, month=sep, pages={977–991} }