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-00000084.xml
Synthesis 2009(15): 2561-2569
DOI: 10.1055/s-0029-1217390
DOI: 10.1055/s-0029-1217390
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Synthesis of the 3C-Protease Inhibitor (-)-Thysanone by a Staunton-Weinreb Annulation Strategy
Further Information
Received
27 February 2009
Publication Date:
08 June 2009 (online)
Publication History
Publication Date:
08 June 2009 (online)
Abstract
The total synthesis of (-)-thysanone is described. The key step involves the addition of an o-toluate anion to a lactone to create the naphthopyran framework (Staunton-Weinreb annulation). This synthesis further confirms the absolute stereochemistry of the natural product to be 1R,3S.
Key words
thysanone - Staunton-Weinreb annulation - total synthesis - natural products - polycycles
- 1
Callahan PL.Mizutani S.Colonno RJ. Proc. Natl. Acad. Sci. U.S.A. 1985, 82: 732 - 2
Binford SL.Maldonado F.Brothers MA.Weady PT.Zalman LS.Meador JW.Matthews DA.Patick AK. Antimicrob. Agents Chemother. 2005, 49: 619 - 3
Singh SB.Cordingley MG.Ball RG.Smith JL.Dombrowski AW.Goetz MA. Tetrahedron Lett. 1991, 32: 5279 - 4 For a recent review on the isolation
and synthesis of pyranonaphthoquinones, see:
Sperry J.Bachu P.Brimble MA. Nat. Prod. Rep. 2008, 25: 376 - 5 For a preliminary communication of
this work, see:
Sperry J.Brimble MA. Synlett 2008, 1910 - For a previous 16-step total synthesis of (-)-thysanone, see:
-
6a
Gill M.Donner CD. Tetrahedron Lett. 1999, 40: 3921 -
6b
Donner CD.Gill M. J. Chem. Soc., Perkin Trans. 1 2002, 938 - For analogue syntheses of thysanone, see:
-
7a
Brimble MA.Elliott RJR.McEwan JF. Aust. J. Chem. 2000, 53: 571 -
7b
Brimble MA.Elliott RJR. Tetrahedron 2002, 58: 183 -
7c
Kraus GA.Ogutu H. Tetrahedron 2002, 58: 7391 -
7d
Bulbule VJ.Koranne PS.Deshpande VH.Borate HB. Tetrahedron 2007, 63: 166 -
7e
Brimble MA.Houghton SI.Woodgate PD. Tetrahedron 2007, 63: 880 -
7f For a formal synthesis
of thysanone, see:
Bachu P.Sperry J.Brimble MA. Tetrahedron 2008, 64: 4827 -
7g
Sawant RT.Waghmode SB. Tetrahedron 2009, 65: 1599 -
8a
Hauser FM.Rhee RP. J. Org. Chem. 1978, 43: 178 -
8b
Kraus GA.Sugimoto H. Tetrahedron Lett. 1978, 19: 2263 - For recent reviews on the Hauser-Kraus annulation, see:
-
9a
Rathwell K.Brimble MA. Synthesis 2007, 5: 643 -
9b
Mal D.Pahari P. Chem. Rev. 2007, 107: 1892 - 10
Kuhn R.Kum K. Chem. Ber. 1962, 95: 2009 - 11
Chiarello J.Jouillé MM. Tetrahedron 1988, 44: 41 - 12
Drochner D.Hüttel W.Bode SE.Müller M.Karl U.Nieger M.Steglich W. Eur. J. Org. Chem. 2007, 1749 - 13
Hauser FM.Rhee RP.Prassana S.Weinreb SM.Dodd JH. Synthesis 1980, 72 - 14
Ramachandran PV.Reddy MVR.Brown HC. Tetrahedron Lett. 2000, 41: 583 - 15
Shao L.Kawano H.Saburi M.Uchida Y. Tetrahedron 1993, 49: 1997 - 16 A previous synthesis of (S)-semivioxanthin methyl ether has been
reported. See:
Deshpande VH.Rai B.Khan RA. Tetrahedron 1996, 52: 7159 -
17a
Evans GE.Leeper FJ.Murphy JA.Staunton J. J. Chem. Soc., Chem. Commun. 1979, 205 -
17b
Dodd JH.Weinreb SM. Tetrahedron Lett. 1979, 38: 3593 - For some recent applications of this annulation in synthesis, see:
-
17c
Zhang Z.Yu B. J. Org. Chem. 2003, 68: 6309 -
17d
Hill B.Rodrigo R. Org. Lett. 2005, 7: 5223 -
17e
Bode SE.Drochner D.Müller M. Angew. Chem. Int. Ed. 2007, 46: 5916 -
17f
Donner CD. Tetrahedron Lett. 2007, 48: 8888 -
17g
Tan NPH.Donner CD. Tetrahedron Lett. 2008, 4160 - 18
Drochner D.Müller M. Eur. J. Org. Chem. 2001, 211 -
19a
Szántay C. Acta Chim. Hung. 1957, 12: 83 -
19b
Banwell MG.Flynn BL.Stewart SG. J. Org. Chem. 1998, 63: 9139