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Synlett 2012(3): 371-374
DOI: 10.1055/s-0031-1290135
DOI: 10.1055/s-0031-1290135
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of Altenusin and Alterlactone
Further Information
Received
27 October 2011
Publication Date:
19 January 2012 (online)
Publication History
Publication Date:
19 January 2012 (online)
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Abstract
The resorcylic lactone alterlactone, a mycotoxin produced by alternaria sp., was synthesized for the first time. The total synthesis was achieved in nine steps with 69% yield starting with acetal-protected phloroglucinic acid and 6-bromopiperonal, where the longest linear sequence consists of five steps. Key step is a Suzuki coupling used for the construction of the central biaryl bond. When the final deprotection with cleavage of benzyl ethers (yielding unprotected alterlactone) was performed in a less polar solvent the biaryl mycotoxin altenusin was obtained.
Key words
polyketides - fungal metabolites - resorcylic lactones - cross-coupling - Suzuki reaction
- Supporting Information for this article is available online:
- Supporting Information
- 1
Bringmann G.Günther C.Ochse M.Schupp O.Tasler S. In Fortschritte der Chemie organischer NaturstoffeHerz W.Falk H.Kirby GW.Moore RE. Springer; Vienna: 2001. p.1-249 -
2a
Handbook of Toxic Fungal Metabolites
Cole RJ.Cox RH. Academic Press; New York: 1981. p.614-645 -
2b
Stinson EE. J. Food Prot. 1985, 48: 80 -
2c
Harvan DJ.Pero RW. In Mycotoxins and other Fungal Related Food ProblemsRodricks JV. American Chemical Society; Washington D.C.: 1976. p.344-355 -
3a
Pero RW.Posner H.Blois M.Harvan D.Spalding JW. Environ. Health Perspect. 1973, 4: 87 -
3b
Davis VM.Stack ME. Appl. Environ. Microbiol. 1994, 60: 3901 -
4a
Combina M.Dalcero A.Varsavsky E.Torres A.Etcheverry M.Rodriguez M.Gonzalez Quintana H. Mycotoxin Res. 1999, 15: 33 -
4b
Tournas VH.Stack ME. J. Food Prot. 2001, 64: 528 -
5a
Harris TM.Hay JV. J. Am. Chem. Soc. 1977, 99: 1631 -
5b
Kanakam CC.Mani NS.Subba Rao GSR. J. Chem. Soc., Perkin Trans. 1 1990, 2233 -
5c
Alo BI.Kandil A.Patil PA.Sharp MJ.Siddiqui MA.Snieckus V.Josephy PD. J. Org. Chem. 1991, 56: 3763 -
5d
Koch K.Podlech J.Pfeiffer E.Metzler M. J. Org. Chem. 2005, 70: 3275 -
6a
Altemöller M.Podlech J.Fenske D. Eur. J. Org. Chem. 2006, 1678 -
6b See also:
Altemöller M.Podlech J. J. Nat. Prod. 2009, 72: 1288 - 7
Altemöller M.Podlech J. Eur. J. Org. Chem. 2009, 2275 - 8
Thomas R. Biochem. J. 1961, 80: 234 -
9a
Ayer WA.Racok JS. Can. J. Chem. 1990, 68: 2085 -
9b
Singh SB.Jayasuriya H.Dewey R.Polishook JD.Zink DL.Dombrowski AW.Guan Z.Collado J.Platas G.Pelaez F.Felock PJ.Hazuda DJ. J. Ind. Microbiol. Biotechnol. 2003, 30: 721 - 10
Oyama M.Xu Z.Lee K.-H.Spitzer TD.Kitrinos P.McDonald OB.Jones RRJ.Garvey EP. Lett. Drug Des. Discovery 2004, 1: 24 - 11
Nakanishi S.Toki S.Saitoh Y.Tsukuda E.Kawahara K.Ando K.Matsuda Y. Biosci. Biotech. Biochem. 1995, 59: 1333 - 12
Uchida R.Tomoda H.Dong Y.Omura S. J. Antibiotics 1999, 52: 572 - 13
Cota BB.Rosa LH.Caligiorne RB.Rabello ALT.Alves TMA.Rosa CA.Zani CL. FEMS Microbiol. Lett. 2008, 285: 177 - 14
Kjer J.Wray V.Edrada-Ebel RA.Ebel R.Pretsch A.Lin W.Proksch P. J. Nat. Prod. 2009, 72: 2053 -
15a
Takahashi S.Kamisuki S.Mizushina Y.Sakaguchi K.Sugawara F.Nakata T. Tetrahedron Lett. 2003, 44: 1875 -
15b
Kamisuki S.Takahashi S.Mizushina Y.Hanashima S.Kuramochi K.Kobayashi S.Sakaguchi K.Nakata T.Sugawara F. Tetrahedron 2004, 60: 5695 -
15c
Kuramochi K.Fukudome K.Kuriyama I.Takeuchi T.Sato Y.Kamisuki S.Tsubaki K.Sugawara F.Yoshida H.Mizushina Y. Bioorg. Med. Chem. 2009, 17: 7227 -
16a
Aly AH.Edrada-Ebel RA.Indriani ID.Wray V.Müller WEG.Totzke F.Zirrgiebel U.Schächtele C.Kubbutat MHG.Lin WH.Proksch P.Ebel R. J. Nat. Prod. 2008, 71: 972 -
16b
Hassan AEHA. PhD Thesis Heinrich-Heine-Universität Düsseldorf; Germany: 2007. -
17a
Ishiyama T.Murata M.Miyaura N. J. Org. Chem. 1995, 60: 7508 -
17b
Murata M.Oyama T.Watanabe S.Masuda Y. J. Org. Chem. 2000, 65: 164 - 18
Altemöller M.Gehring T.Cudaj J.Podlech J.Goesmann H.Feldmann C.Rothenberger A. Eur. J. Org. Chem. 2009, 2130 -
19a
Chandrasekhar S.Reddy NR.Rao YS. Tetrahedron 2006, 62: 12098 -
19b
Kuenburg B.Czollner L.Frohlich J.Jordis U. Org. Process Res. Dev. 1999, 3: 425 -
20a
Reitz A.Avery MA.Verlander MS.Goodman M. J. Org. Chem. 1981, 46: 4859 -
20b
Bhakuni DS.Kumar P. J. Indian Chem. Soc. 1988, 6: 417 -
20c
Vickery EH.Pahler LF.Eisenbraun EJ. J. Org. Chem. 1979, 44: 4444 -
20d
Tatsuta K.Furuyama A.Yano T.Suzuki Y.Ogura T.Hosokawa S. Tetrahedron Lett. 2008, 49: 4036 - 21
Henry TA.Sharp TM. J. Chem. Soc. 1930, 2279 -
22a
Suzuki A. Proc. Jpn. Acad. 2004, 80: 359 -
22b
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 -
22c
Alonso F.Beletskaya IP.Yus M. Tetrahedron 2008, 64: 3047 -
22d
Martin R.Buchwald SL. Acc. Chem. Res. 2008, 41: 1461