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DOI: 10.1055/s-2007-990866
Stereoselective Total Synthesis of Bioactive Styryllactones: 9-Deoxygoniopypyrone, Goniopypyrone and 7-epi-Goniofufurone
Publication History
Publication Date:
31 October 2007 (online)
Abstract
Stereoselective synthesis of the bioactive styryllactones (+)-9-deoxygoniopypyrone, (+)-goniopypyrone and (+)-7-epi-goniofufurone has been achieved from d-(-)-tartaric acid. The key step involves the elaboration of a trihydroxy ester to the title compounds utilizing high-yielding stereoselective transformations.
Key words
styryllactone - goniopypyrone - 7-epi-goniofufurone - tartaric acid
- For reviews on the cytotoxic activity and other bioactivity of styryllactones, see:
- 1a
Mereyala HB.Joe M. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1: 293 - 1b
Blázquez MA.Bermejo A.Zafra-Polo MC.Cortes D. Phytochem. Anal. 1999, 10: 161 - 2 For a review on the synthesis of styryllactones until 2004, see:
Mondon M.Gesson J.-P. Curr. Org. Synth. 2006, 3: 41 - 3a
Prasad KR.Gholap SL. Synlett 2005, 2260 - 3b
Prasad KR.Gholap SL. J. Org. Chem. 2006, 71: 3643 - 3c
Prasad KR.Anbarasan P. Tetrahedron: Asymmetry 2005, 16: 3951 - 3d
Prasad KR.Anbarasan P. Tetrahedron Lett. 2006, 47: 1433 - 3e
Prasad KR.Anbarasan P. Synlett 2006, 2087 - 3f
Prasad KR.Anbarasan P. Tetrahedron: Asymmetry 2006, 17: 1146 - 3g
Prasad KR.Anbarasan P. Tetrahedron 2006, 62: 8303 - 3h
Prasad KR.Chandrakumar A.Anbarasan P. Tetrahedron: Asymmetry 2006, 17: 1979 - 4 Preliminary communication:
Prasad KR.Dhaware MG. Synlett 2007, 1112 - For recent syntheses of 9-deoxygoniopypyrone, see:
- 5a
Yamashita Y.Saito S.Kobayashi S. J. Am. Chem. Soc. 2003, 125: 3793 - 5b
Ramachandran PV.Chandra JS.Reddy MVR. J. Org. Chem. 2002, 67: 7547 - 5c
Chen J.Lin G.-Q.Wang Z.-M.Liu H.-Q. Synlett 2002, 1265 - 5d
Tsubaki M.Kanai K.Nagase H.Honda T. Tetrahedron 1999, 55: 2493 - 5e
Survivet J.-P.Vitale J.-M. Tetrahedron 1999, 55: 13011 - 5f
Mukai C.Hirai S.Hanaoka M. J. Org. Chem. 1997, 62: 6619 - For syntheses of goniopypyrone, see:
- 6a
Shing TKM.Tsui HC.Zhou ZH. Tetrahedron Lett. 1993, 34: 691 - 6b
Zhou W.-S.Yang Z.-C. Tetrahedron Lett. 1993, 34: 7075 - 6c
Surivet J.-P.Vatele J.-M. Tetrahedron Lett. 1997, 38: 819 - 6d
Li H.-M.Yang M.Zhao G.Yu Q.-S.Ding Y. Chin. J. Chem. 2000, 18: 388 - For the isolation of goniofufurone and 7-epi-goniofufurone, see:
- 8a
Fang X.-P.Anderson JE.Chang C.-J.McLaughlin JL.Fanwick PE. J. Nat. Prod. 1991, 54: 1034 - 8b
Fang X.-P.Anderson JE.Chang C.-J.Fanwick PE.McLaughlin JL. J. Chem. Soc., Perkin Trans. 1 1990, 1655 - For syntheses of goniofufurone and 7-epi-goniofufurone, see:
- 8c
Shing TKM.Tsui HC.Zhou ZH. Tetrahedron 1992, 48: 8659 - 8d
Prakash KRC.Rao SP. Tetrahedron 1993, 49: 1505 - 8e
Ye J.Bhatt RK.Falck JR. Tetrahedron Lett. 1993, 34: 8007 - 8f
Gracza T.Jaeger V. Synthesis 1994, 1359 - 8g
Yang Z.-C.Zhou W.-S. Tetrahedron 1995, 51: 1429 - 8h
Mukai C.Hirai S.Kim IJ.Masaru K.Hanaoka M. Tetrahedron 1996, 52: 6547 - 8i
Yi X.-H.Meng Y.Hua X.-G.Li C.-J. J. Org. Chem. 1998, 63: 7472 - 8j
Bruns R.Wernicke A.Koll P. Tetrahedron 1999, 55: 9793 - 8k
Mereyala HB.Gadikota RR. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39: 166 - 8l
Su Y.-L.Yang C.-S.Teng S.-J.Zhao G.Ding Y. Tetrahedron 2001, 57: 2147 - 8m
Ruiz P.Murga J.Carda M.Marco JA. J. Org. Chem. 2005, 70: 713 - 8n
Fernanndez de la Pradilla R.Fernandez J.Alma V.Fernanndez J.Gomez A. Heterocycles 2006, 68: 1579 - 9
Shing TKM.Tsui HC.Zhou ZH. J. Org. Chem. 1995, 60: 3121
References
The diastereomeric ratio (5:1) of the formed alcohols was estimated by 1H NMR spectroscopy. The stereochemistry of the alcohols was further corroborated by conversion into the natural product. Following a sequence that is outlined for goniopypyrone, the major product obtained in the addition of vinylmagnesium bromide to aldehyde 17 was converted into 9-epi-goniopypyrone in 10.5% overall yield starting from trihydroxy ester (Scheme [6] ).
Scheme 6