RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012(3): 362-371
DOI: 10.1055/s-0031-1289651
DOI: 10.1055/s-0031-1289651
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Second-Generation Synthesis of (-)-Viriditoxin
Weitere Informationen
Received
8 November 2011
Publikationsdatum:
16. Januar 2012 (online)
Publikationsverlauf
Publikationsdatum:
16. Januar 2012 (online)
Abstract
Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.
Key words
natural products - asymmetric synthesis - antibiotics - atropisomerism - biaryls
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0024th:
- Primary Data
- 1
Lock RL.Harry EJ. Nat. Rev. Drug Discovery 2008, 7: 324 - 2
Erickson HP.Anderson DE.Osawa M. Microbiol. Mol. Biol. Rev. 2010, 74: 504 -
3a
RayChaudhuri D.Park JT. Nature (London) 1992, 359: 251 -
3b
De Boer P.Crossley R.Rothfield L. Nature (London) 1992, 359: 254 -
3c
Mukherjee A.Dai K.Lutkenhaus J. Proc. Natl. Acad. Sci. U.S.A. 1993, 90: 1053 -
3d
Foss M.Eun Y.-J.Weibel D. B. Biochemistry 2011, 50: 7719 - 4
Weisleder D.Lillehoj EB. Tetrahedron Lett. 1971, 12: 4705 - 5
Suzuki K.Nozawa K.Nakajima S.Kawai K. Chem. Pharm. Bull. 1990, 38: 3180 - 6
Wang J.Galgoci A.Kodali S.Herath KB.Jayasuriya H.Dorso K.Vicente F.Gonzalez A.Cully D.Bramhill D.Singh S. J. Biol. Chem. 2003, 278: 44424 - 7
Hood RD.Hayes AW.Scammell JG. Food Cosmet. Toxicol. 1976, 14: 175 - 8
Arone A.Assante G.Montorsi M.Nasini G. Phytochemistry 1995, 38: 595 - 9
Elix JA.Wardlaw JH. Aust. J. Chem. 2004, 57: 681 - 10
Suzuki K.Nozawa K.Nakajima S.Udagawa S.Kawai K. Chem. Pharm. Bull. 1992, 40: 1116 -
11a
Ng AS.Just G.Blank F. Can. J. Chem. 1969, 47: 1223 -
11b
Blank F.Ng AS.Just G. Can. J. Chem. 1966, 44: 2873 -
12a
Matsumoto M.Minato H.Kondo E.Mitsugi T.Katagiri K. J. Antibiot. 1975, 28: 602 -
12b
Koyama K.Natori S.Iitaka Y. Chem. Pharm. Bull. 1987, 35: 4049 -
13a
Gill M. Nat. Prod. Rep. 2003, 20: 615 -
13b
Isaka M.Kittakoop P.Kirtikara K.Hywel-Jones NL.Thebtaranonth Y. Acc. Chem. Res. 2005, 38: 813 -
13c
Sperry J.Bachu P.Brimble MA. Nat. Prod. Rep. 2008, 25: 376 -
14a
Bringmann G.Gulder T.Gulder TAM.Breuning M. Chem. Rev. 2011, 111: 563 -
14b
Kozlowski MC.Morgan BJ.Linton EC. Chem. Soc. Rev. 2009, 38: 3193 - 15
Park YS.Grove CI.González-López M.Urgaonkar S.Fettinger JC.Shaw JT. Angew. Chem. Int. Ed. 2011, 50: 3730 - 16
Bode SE.Drochner D.Mueller M. Angew. Chem. Int. Ed. 2007, 46: 5916 - 17
Romaine IM.Hempel JE.Shanmugam G.Hori H.Igarashi Y.Polavarapu PL.Sulikowski GA. Org. Lett. 2011, 13: 4538 - 18
Coleman RS.Grant EB. J. Am. Chem. Soc. 1995, 117: 10889 - 19
Kozlowski MC.Dugan EC.DiVirgilio ES.Maksimenka K.Bringmann G. Adv. Synth. Catal. 2007, 349: 583 - 20
Volkmann RA.Kelbaugh PR.Nason DM.Jasys VJ. J. Org. Chem. 1992, 57: 4352 - 21
Shen R.Inoue T.Forgac M.Porco JA. J. Org. Chem. 2005, 70: 3686 - 22
Murata T.Sano M.Takamura H.Kadota I.Uemura D. J. Org. Chem. 2009, 74: 4797 - 23
Bolla ML.Patterson B.Rychnovsky SD. J. Am. Chem. Soc. 2005, 127: 16044 - 24
Dalgard JE.Rychnovsky SD. Org. Lett. 2005, 7: 1589 -
25a
Evans GE.Leeper FJ.Murphy JA.Staunton J. J. Chem. Soc., Chem. Commun. 1979, 205 -
25b
Dodd JH.Weinreb SM. Tetrahedron Lett. 1979, 20: 3593 - 26
Tan NPH.Donner CD. Tetrahedron 2009, 65: 4007 - 27
Ferguson ML.O’Leary DJ.Grubbs RH. Org. Synth. 2003, 80: 85 - 29
Brockway AJ.Gonzalez-Lopez M.Fettinger JC.Shaw JT. J. Org. Chem. 2011, 76: 3515 - 30
Miyake H.Tsumura T.Sasaki M. Tetrahedron Lett. 2004, 45: 7213 - 31
Han JH.Kwon YE.Sohn J.-H.Ryu DH. Tetrahedron 2010, 66: 1673 - 32
Guo Q.-X.Wu Z.-J.Luo Z.-B.Liu Q.-Z.Ye J.-L.Luo S.-W.Cun L.-F.Gong L.-Z. J. Am. Chem. Soc. 2007, 129: 13927 - 33
Armarego WLF.Chai C. Purification of Laboratory Chemicals 5th ed.: Butterworth Heinemann; Oxford: 2003. p.608
References
Crystallographic data for compound 9 have been submitted to Cambridge Crystallographic Database and assigned deposition number CCDC 858638.