Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2006(13): 1975-2000
DOI: 10.1055/s-2006-948193
DOI: 10.1055/s-2006-948193
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Electrocyclic Ring-Opening Reactions of gem-Dibromocyclopropanes in the Synthesis of Natural Products and Related Compounds
Further Information
Received
22 March 2006
Publication Date:
09 August 2006 (online)
Publication History
Publication Date:
09 August 2006 (online)
Abstract
The disrotatory ring opening of gem-dibromocyclopropanes provides a versatile and increasingly utilised procedure for the synthesis of a range of natural products. The field is summarised and product formation explained.
-
1 Introduction
-
2 Selected Uses of gem-Dibromocyclopropanes
-
2.1 Via the Lithium Bromocarbenoid
-
2.2 Via the 1-Bromocyclopropene
-
2.3 Miscellaneous Transformations
-
3 The Cyclopropyl-to-Allyl Rearrangement
-
3.1 Mechanistic Aspects
-
3.2 Thermal Reactions
-
3.3 Reactions in the Presence of an External Nucleophile
-
3.3.1 Non-Annelated gem-Dibromocyclopropanes
-
3.3.2 Medium-to-Large Ring-Fused gem-Dibromocyclopropanes
-
3.3.3 7,7-Dibromobicyclo[4.1.0]heptanes
-
3.3.4 6,6-Dibromobicyclo[3.1.0]hexanes
-
3.4 Reactions in the Presence of an Internal Nucleophile
-
3.4.1 Attached Directly to the Cyclopropane
-
3.4.2 Attached to a Remote Centre
Key words
dibromocyclopropanes - disrotatory openings - allylic cations - natural products - total synthesis
- 1
Kostikov RR.Molcahnov AP. Top. Curr. Chem. 1990, 155: 41 - 3
Fedorynski M. Chem. Rev. 2003, 103: 1099 - 4
The Chemistry of the Functional Groups: The Cyclopropyl Group
Vol. 2:
Wiley Interscience;
Chichester:
1995.
- 5
Léonel E.Lejaye M.Oudeyer S.Paugam JP.Nedelec J.-Y. Tetrahedron Lett. 2004, 45: 2635 -
6a
Reissig H.-U. In The Chemistry of the Functional Groups: The Cyclopropyl Group Part 1:Rappoport Z. Wiley Interscience; Chichester, UK: 1987. p.410 -
6b
Weyerstahl P. In The Chemistry of the Functional Groups: The Chemistry of Halides, Pseudohalides and Azides Suppl. D:Rappoport Z.Patai S. Wiley Interscience; Chichester UK: 1983. p.1451 -
6c
Barlet R.Vo-Quang Y. Bull. Soc. Chim. Fr. 1969, 3729 - 7
Banwell MG.Reum ME. In Advances in Strain in Organic Chemistry Vol. 1:Halton B. JAI Press; London: 1991. p.19 - 8
Baird MS. In Advances in Strain in Organic Chemistry Vol. 1:Halton B. JAI Press; London: 1991. p.65 - 9
Sydnes LK.Bakstad E. In Advances in Strain in Organic Chemistry Vol. 5:Halton B. JAI Press; Greenwich, Connecticut: 1996. p.85 - 10
Sydnes LK. Chem. Rev. 2003, 103: 1133 - 11
Tanabe Y.Nishii Y. J. Synth. Org. Chem. Jpn. 1999, 57: 170 - 12
Nilsen NO.Skattebol L.Baird MS.Buxton SR.Slowey PD. Tetrahedron Lett. 1984, 25: 2887 - 13
Pellicciari R.Raimondo M.Marinozzi M.Natalini B.Costantino G.Thomsen C. J. Med. Chem. 1996, 39: 2874 -
14a
Page PCB.Jennens DC.McFarland H. Tetrahedron Lett. 1997, 38: 6913 -
14b
Jenniskens LHD.Wijnberg JBPA.De Groot A. J. Org. Chem. 1991, 56: 6585 - 15
Kamata S.Haga N.Tsuri T.Uchida K.Kakushi H.Arita H.Hanasaki K. J. Med. Chem. 1990, 33: 229 -
16a
Inoue A.Kondo J.Shinokubo H.Oshima K. Chem. Eur. J. 2002, 8: 1730 -
16b
Inoue R.Shinokubo H.Oshima K. Tetrahedron Lett. 1996, 37: 5377 -
17a
Winkler JD.Rouse MB.Greaney MF.Harrison SJ.Jeon YT. J. Am. Chem. Soc. 2002, 124: 9726 -
17b
Cha JK.Epstein OL. Tetrahedron 2006, 62: 1329 - 18
Drew MGB.Harwood LM.Macias-Sanchez AJ.Scott R.Thomas RM.Uguen D. Angew. Chem. Int. Ed. 2001, 40: 2311 - 19
Kawauchi H. inventors; JP 98-64319, 11246563. ; Chem. Abstr. 1999, 131, 199936 - 20
Banwell MG.Cowden CJ.Gravatt GL.Rickard CEF. Aust. J. Chem. 1993, 46: 1941 - 21
Banwell MG.Cameron JM.Collis MP.Gravatt GL. Aust. J. Chem. 1997, 50: 395 -
22a
Banwell MG.Lambert JN.Gravatt GL. J. Chem. Soc., Perkin Trans. 1 1993, 2817 -
22b
Banwell MG.Gravatt GL.Buckleton JS.Clark GR.Rickard CEF. J. Chem. Soc., Chem. Commun. 1989, 865 - 23
Baker WR.Jae HS.Martin SF.Condon SL.Stein HH.Cohen J.Kleinert HD. Bioorg. Med. Chem. Lett. 1992, 2: 1405 - 24
Al Dulayymi JR.Baird MS.Bolesov IG.Nizovtsev AV.Tverezovsky VV. J. Chem. Soc., Perkin Trans. 2 2000, 1603 - 25
Detert H.Meier H. Liebigs Ann./Recl. 1997, 1557 - 26
Klimova EI.Meleshonkova NN.Klimova TB.Martinez MG.Alvarez CT. Mendeleev Commun. 1997, 241 - 27
Hirao T.Hirano K.Hasegawa T.Ohshiro Y.Ikeda I. J. Org. Chem. 1993, 58: 6529 -
28a
Harada T.Katsuhira T.Hattori K.Oku A. J. Org. Chem. 1993, 58: 2958 -
28b
Harada T.Katsuhira T.Hattori K.Oku A. Tetrahedron Lett. 1989, 30: 6039 - 29
Banwell MG.Halton B. In The Chemistry of the Functional Groups: The Cyclopropyl Group Part 2:Rappoport Z. Wiley Interscience; Chichester UK: 1987. p.1223 - 30
Al-Dulayymi AR.Al-Dulayymi JR.Baird MS.Gerrard ME.Koza G.Harkins SD.Roberts E. Tetrahedron 1996, 52: 3409 - 31
Al-Dulayymi JR.Baird MS. J. Chem. Soc., Perkin Trans. 1 1994, 1547 - 32
Al-Dulayymi JR.Baird MS. Tetrahedron 1990, 46: 5703 - 33
Baird MS.Dale CM.Lytollis W.Simpson MJ. Tetrahedron Lett. 1992, 33: 1521 -
34a
Bakstad E.Olsen AS.Sandberg M.Sydnes LK. Acta Chem. Scand. 1999, 53: 465 -
34b
Sydnes LK.Bakstad E. Acta Chem. Scand. 1996, 50: 446 -
35a
Kostikov RR.Varakin GS.Molchanov AP.Ogloblin KA. Zh. Org. Khim. 1996, 32: 39 -
35b
Kostikov RR.Varakin GS.Molchanov AP.Ogloblin KA. Zh. Org. Khim. 1996, 32: 33 - 36
Ishihara T.Kudaka T.Ando T. Tetrahedron Lett. 1984, 25: 4765 - 37
Siginova LG.Al’khamdan M.Petrosyan VS. Vestn. Mosk. Univ., Ser 2: Khim. 1995, 36: 573 ; Chem. Abstr. 1996, 124, 288884 -
38a
Lin S.-T.Kuo S.-H.Yang F.-M. J. Org. Chem. 1997, 62: 5229 -
38b
Lin L.-H.Lin S.-T.Yang H.-J. J. Chin. Chem. Soc. (Taipei) 1998, 45: 193 ; Chem. Abstr. 1998, 128, 243979 - 39
Lown JW. Rev. React. Species Chem. React. 1975, 1: 89 - 40
Marvell EN. Thermal Electrocyclic Reactions Academic Press; New York: 1980. -
41a
White JD.Lee NC. In Advances in Strain in Organic Chemistry Vol. 6:Halton B. JAI Press; Greenwich, CN: 1997. p.1 -
41b
Moore HW.Xerxa BR. In Advances in Strain in Organic Chemistry Vol. 4:Halton B. JAI Press; Greenwich, CN: 1995. p.81 - 42
Roberts JD.Chambers VC. J. Am. Chem. Soc. 1951, 73: 5034 - 43
Christol SF.Seguira RM.DePuy CH. J. Am. Chem. Soc. 1965, 87: 4006 - 44
DePuy CH.Schnack LG.Hausser JW.Wiedeman W. J. Am. Chem. Soc. 1967, 89: 4006 - 45
Woodward RB.Hoffmann R. The Conservation of Orbital Symmetry Academic Press; New York: 1970. -
46a
Wolk JL.Sprecher M.Basch H.Hoz S. Org. Biomol. Chem. 2004, 2: 1065 -
46b
Sella A.Basch H.Hoz S. J. Am. Chem. Soc. 1996, 118: 416 - 47
Faza ON.Lopez CS.Alvarez R.de Lera AR. J. Org. Chem. 2004, 69: 9002 - 48
Sandler SR. Chem. Ind. (London) 1968, 1481 -
49a
Ioffe AI.Nefedov OM. Izv. Akad. Nauk SSSR, Ser. Khim. 1974, 1536 ; Chem. Abstr. 1975, 81, 104431 -
49b
Grob CA.Pfaendler HR. Helv. Chim. Acta 1970, 53: 2130 - 50
Baird MS.Lindsay DG.Reese CB. J. Chem. Soc. C 1969, 1173 - 51
Werstiuk NH.Roy CD.Ma J. Can. J. Chem. 1994, 72: 2537 - 52
Werstiuk NH.Roy CD. Tetrahedron Lett. 2001, 42: 3255 - 53
Gassman PG.Han S.Chyall LJ. Tetrahedron Lett. 1998, 39: 5459 - 54
Ceylan M.Budak Y. J. Chem. Res., Synop. 2002, 416 - 55
Bentley TW.Norman SJ.Kemmer R.Christl M. Liebigs Ann. 1995, 599 - 56
Weber J.Xu L.Brinker UH. Tetrahedron Lett. 1992, 33: 4537 -
57a
Kostitsyn AB.Shulishov EV.Tomilov YV.Nefedov OM.Zelinskii ND. Synlett 1990, 713 -
57b
Molchanov AP.Pecheritsyna YP.Kostikov RR. Zh. Org. Khim. 1989, 25: 1195 -
57c
Slobodin YM.Ashkinazi LA.Shustareva TK. Zh. Org. Khim. 1983, 19: 2062 - 58
Shkuro OA.Nikitina LE.Plemenkov VV.Strunskaya EI. Russ. J. Org. Chem. 1997, 33: 835 - 59
Hickey ER.Paquetter LA. J. Am. Chem. Soc. 1995, 117: 163 -
60a
Skatterbol L. J. Org. Chem. 1964, 29: 2951 -
60b
Holm KH.Skatteboel L. Acta Chem. Scand. 1985, 39: 549 ; and references cited therein -
61a
Asahara T.Ono K.Tanaka K. Bull. Chem. Soc. Jpn. 1971, 44: 1130 -
61b
Baird MS,Mahli BS, andSheppard L. inventors; GB 90-14824, 2245560. ; Chem. Abstr. 1992, 116, 193696 - 62
Molchanov AP.Kostikov RR. Zh. Org. Khim. 1989, 25: 2533 - 63
Baird MS.Mahli BS.Sheppard L. J. Chem. Soc., Perkin Trans. 1 1990, 1881 -
64a
Magnus P.Westwood N.Spyvee M.Frost C.Linnane P.Tavares F.Lynch V. Tetrahedron 1999, 55: 6435 -
64b
Frost C.Linnane P.Magnus P.Spyvee M. Tetrahedron Lett. 1996, 37: 9139 - 65
Laurent A.Villalva-Servin NP.Forgione P.Wilson PD.Smil DV.Fallis AG. Can. J. Chem. 2004, 82: 215 - 66
Stec MM.Gwaltney SL.Burke LD.Nguyen H.Shea KJ. Tetrahedron Lett. 2003, 44: 9379 - 67
Banwell MG.Lambert JN.Reum ME.Onrust R. Org. Prep. Proced. Int. 1988, 20: 393 - 68
Morin Deveau A.Macdonald TL. Tetrahedron Lett. 2004, 45: 803 - 69
Banwell MG.Dupuche JR. Aust. J. Chem. 1994, 47: 203 - 70
Banwell MG.Collis MP.Mackay MF.Richards SL. J. Chem. Soc., Perkin Trans. 1 1993, 1913 - 71
Banwell MG.Corbett M.Mackay MF.Richards SL. J. Chem. Soc., Perkin Trans. 1 1992, 1329 - 72
Sandler SR. J. Org. Chem. 1967, 32: 3867 - 73
Molchanov AP.Kostikov RR. Zh. Org. Khim. 1993, 29: 510 - 74
Sandler SR. Org. Synth. 1977, 56: 32 - 75
Kitatani K.Hiyama T.Nozaki H. Bull. Chem. Soc. Jpn. 1977, 50: 3288 - 76
Baird MS.Hussain HH. J. Chem. Res., Synop. 1988, 292 - 77
Sandler SR. J. Org. Chem. 1968, 33: 4537 - 78
Kostikov RR.Varakin GS.Molchanov AP.Ogloblin KA. Zh. Org. Khim. 1996, 32: 367 - 79
Hayes JF.Shipman M.Slawin AMZ.Twin H. Heterocycles 2002, 58: 243 -
80a
Korneva OS.Menchikov LG.Kolytun ES.Nefedov OM. Mendeleev Commun. 1995, 135 -
80b
Korneva OS.Nefedov OM. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2518 ; Chem. Abstr. 1992, 116, 58780 - 81
Weng WW.Yau Luh T. J. Chem. Soc., Perkin Trans. 1 1993, 2687 -
82a
Nerdel F.Hentschel P.Brodowski W.Buddrus J. Justus Liebigs Ann. Chem. 1971, 746: 6 -
82b
Weyerstahl P.Klamann D.Finger C.Fligge M.Nerdel F.Buddrus J. Chem. Ber. 1968, 101: 1303 - 83
Leandri G.Monti H.Bertrand M. Tetrahedron 1974, 30: 283 - 84
Kiselev MY.Kostikov RR.Molchanov AP. Zh. Org. Khim. 1990, 26: 1005 - 85
Banwell MG.Sydnes MO. Aust. J. Chem. 2004, 57: 537 - 86
Banwell MG.Beck DAS.Stanislawski PC.Sydnes MO.Taylor RM. Curr. Org. Chem. 2005, 9: 1589 - 87
Banwell MG.Edwards AJ.Jolliffe KA.Smith JA.Hamel E.Verdier-Pinard P. Org. Biomol. Chem. 2003, 1: 296 - 88
Parham WE.Sperley RJ. J. Org. Chem. 1967, 32: 924 - 89
Loozen HJJ.De Haan JW.Buck HM. J. Org. Chem. 1977, 42: 418 - 90
Loozen HJJ.Robben WMM.Richter TL.Buck HM. J. Org. Chem. 1976, 41: 384 - 91
Loozen HJJ.Robben WMM.Buck HM. Recl. Trav. Chim. Pays-Bas 1976, 95: 248 - 92
Murphy JA.Scott KA.Sinclair RS.Lewis N. Tetrahedron Lett. 1997, 38: 7295 - 93
Danheiser RL.Morin JM.Salaski EJ. J. Am. Chem. Soc. 1985, 107: 8066 - 94
Trost BM.Oslob JD. J. Am. Chem. Soc. 1999, 121: 3057 - 95
Arct J.Prawda A.Kozyriev V. Bull. Acad. Pol. Sci., Ser. Chim. 1978, 26: 523 ; Chem. Abstr. 1979, 26, 38247 - 96
Laplanche A.Kerfanto M. C. R. Seances Acad. Sci., Ser. C 1970, 271: 1462 ; Chem. Abstr. 1971, 74, 53144 - 97
Brocksom TJ.Pesquero ETC.Lopes FT. Synth. Commun. 1990, 20: 1181 - 98
Chuiko VA.Manukov EN.Yaremchenko NG. Vestsi Akad. Navuk Belarusi, Ser. Khim. Navuk 1996, 70 ; Chem. Abstr. 1977, 127, 50118 -
99a
Vorogushin AV.Wulff WD.Hansen H.-J. J. Am. Chem. Soc. 2002, 124: 6512 -
99b
Vorogushin AV.Wulff WD.Hansen H.-J. Org. Lett. 2001, 3: 2641 - 100
Kato M.Mitsuda M.Tatsumoto T.Uchida R.Ichimura A. Chem. Lett. 1989, 1789 - 101
Dehmlow E.Groening C. Tetrahedron 1992, 48: 111 - 102
Wessjohann LA.Muhlbauer A.Sinks U. Acta Chem. Scand. 1997, 51: 1112 -
103a
Banwell MG.Cowden CJ. Aust. J. Chem. 1994, 47: 2235 -
103b
Banwell MG.Cowden CJ.Mackay MF. J. Chem. Soc., Chem. Commun. 1994, 61 - 105
Azadi-Ardakani M.Wallace TW. Electr. Conf. Trends Org. Chem. [CD ROM]Rzepa H.Leach C.Goodman JM. RSC; Cambridge, UK: 1996. Paper 28; Chem. Abstr. 1996, 125, 10225 - 106
Banwell MG.Cowden CJ.Gable RW. J. Chem. Soc., Perkin Trans. 1 1994, 3515 - 107
Banwell MG.Ebenbeck W.Edwards AJ. J. Chem. Soc., Perkin Trans. 1 2001, 114 - 108
Zhang L.Koreeda M. Org. Lett. 2004, 6: 537 - 109
Wijsman GW.De Wolf WH.Bickelhaupt F.Kooijman H.Spek AL. J. Am. Chem. Soc. 1992, 114: 9191 - 110
Bickelhaupt F.De Wolf WH. In Advances in Strain in Organic Chemistry Vol. 3:Halton B. JAI Press; London: 1993. p.185 -
111a
Kagabu S.Ando C.Ando J. J. Chem. Soc., Perkin Trans. 1 1994, 739 -
111b
Kagabu S.Tsuji H.Kawai I.Ozeki H. Bull. Chem. Soc. Jpn. 1995, 68: 341 - 112
Anderson JC.Lindsay DG.Reese CB. Tetrahedron 1964, 20: 2091 - 113
Skatteboel L. J. Org. Chem. 1970, 35: 3200 - 114
Kirsch V.Wolff C.Nather C.Tochtermann W. Eur. J. Org. Chem. 2000, 1741 - 115
Cousins GS.Hoberg JO. In Advances in Strained and Interesting Organic Molecules Vol. 8:Halton B. JAI Press; Stamford, CN: 2000. p.113 - 116
Ramana CV.Murali R.Nagarajan M. J. Org. Chem. 1997, 62: 7694 - 117
Anderson AGJ.Murph BT. Org. Prep. Proced. Int. 1992, 24: 478 - 118
Banwell MG.Berak M.Hockless DCR. J. Chem. Soc., Perkin Trans. 1 1996, 2217 - 119
Banwell MG.Gable RW.Peters SC.Phyland JR. J. Chem. Soc., Chem. Commun. 1995, 1395 -
120a
Miller TA.Bulman AL.Thompson CD.Garst ME.Macdonald TL. J. Med. Chem. 1997, 40: 3836 -
120b
Miller TA.Bulman AL.Thompson CD.Garst ME.Macdonald TL. Bioorg. Med. Chem. Lett. 1997, 7: 1851 -
120c
Garst ME, andMacDonald TL. inventors; WO 98-US4711, 9840077. ; Chem. Abstr. 1998, 129, 230883 - 121
Fokin AA.Butova ED.Kolomitsin IV.Gagaeva EA.Goroman IV.Kornilov AM.Sorochinskii AE.Yurchenko AG.Krasutskii PA. Zh. Org. Khim. 1994, 30: 669 - 122
Wenkert E.Arrhenius TS.Bookser B.Guo M.Mancini P. J. Org. Chem. 1990, 55: 1185 - 123
Kirihara M.Kambayashi T.Momose T. Chem. Commun. 1996, 1103 - 124
Kirihara M.Kakuda H.Tsunooka M.Shimajiri A.Takuwa T.Hatano A. Tetrahedron Lett. 2003, 44: 8513 - 125
McCullough KJ.MacTavish J.Proctor GR.Redpath J. J. Chem. Soc., Perkin Trans. 1 1996, 2553 - 126
Lantos I.Katerinopoulos HE. Can. J. Chem. 1991, 69: 1033 - 127
Danheiser RL.Morin JM.Yu M.Basak A. Tetrahedron Lett. 1981, 22: 4205 -
128a
Sydnes LK.Mungaroo R.Svendsen JS. Acta Chem. Scand. 1998, 52: 1392 -
128b
Sydnes LK.Mungaroo R.Aanesen BA. Acta Chem. Scand. 1998, 52: 1386 -
128c
Svendsen JS.Sydnes LK. Acta Chem. Scand. 1990, 44: 202 -
128d
Hemmingsen TH.Svendsen JS.Sydnes LK. Acta Chem. Scand., Ser. B 1988, 42: 651 - 129
Banwell MG.Harvey JE.Hockless DCR.Wu AW. J. Org. Chem. 2000, 65: 4241 - 130
Banwell MG.Wu AW. J. Chem. Soc., Perkin Trans. 1 1994, 2671 - 131
Harvey J. PhD Thesis Australian National University; Australia: 2000. - 132
Banwell MG.Harvey JE.Jolliffe KA. J. Chem. Soc., Perkin Trans. 1 2001, 2002 - 133
Banwell M.Edwards A.Harvey J.Hockless D.Willis A. J. Chem. Soc., Perkin Trans. 1 2000, 2175 - 134
Stanislawski PC.Willis AC.Banwell MG. Org. Lett. 2006, 8: 2143 - 135
Gassman PG.Tan L.Hoye TR. Tetrahedron Lett. 1996, 37: 439
References
Special issue on cyclopropanes and related rings: Chem. Rev.; 2003, 103 (4).
104Banwell, M. G.; Ma, X. 2006, in preparation. We thank Professor Banwell for providing this information prior to publication.