Triphenylphosphine-Promoted Synthesis of Spiroketals from Phthalic Anhydride with Dialkyl Acetylenedicarboxylates

REFERENCES

• (a) Paterson , I. ; Anderson , E. A. The renaissance of natural products as drug candidates . Science 2005 , 310 , 451 – 453 ; (b) Dervon , T. K. ; Scott , A. I. Handbook of Naturally Occurring Compounds; Academic: New York, 1972; Vol. II . (c) Collins , I. Saturated and unsaturated lactones . J. Chem. Soc., Perkin Trans. 1 1999 , 1377 – 1396 ; (d) Hibino , S. ; Choshi , T. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit . Nat. Prod. Rep. 2002 , 19 , 148 – 180 ; (e) Trost , B. M. ; Balkoves , J. M. ; Mao , M. K. T. A biomimetic approach to plumericin . J. Am. Chem. Soc. 1983 , 105 , 6755 – 6757 .
   PubMed Web of Science ®Google Scholar
• Reviews about spiroketals, see: (a) Yeung , K. S. ; Paterson , I. Advances in the total synthesis of biologically important marine macrolides . Chem. Rev. 2005 , 105 , 4237 – 4313 ; (b) Perron , F. ; Albizati , K. F. Chemistry of spiroketal . Chem. Rev. 1989 , 89 , 1617 – 1661 ; (c) Brasholz , M. ; Sörgel , S. ; Azap , C. ; Reibig , H. U. Rubromycins: Structurally intriguing, biologically valuable, synthetically challenging antitumour antibiotics . Eur. J. Org. Chem. 2007 , 3801 – 3814 .
   PubMed Web of Science ®Google Scholar
• (a) Ueki , T. ; Doe , M. ; Tanaka , R. ; Morimoto , Y. ; Yoshihara , K. ; Kinoshita , T. Total synthesis of hyperolactones A, B and C . J. Heterocycl. Chem. 2001 , 38 , 165 – 172 ; (b) Cuzzupe , A. N. ; Di Florio , R. ; Rizzacasa , M. A. Enantiospecific synthesis of the phospholipase A2 inhibitor (−)-cinatrin . J. Org. Chem. 2002 , 67 , 4392 – 4398 .
   Web of Science ®Google Scholar
• For design and synthesis of spiroketal derivatives, see: (a) Zinzalla , G. ; Milroy , L. G. ; Ley , S. V. Chemical variation of natural product-like scaffolds: Design and synthesis of spiroketal derivatives . Org. Biomol. Chem. 2006 , 4 , 1977 – 2002 ; (b) Iglesias-Arteaga , M. A. ; Simuta-Lopez , E. M. ; Xochihua-Moreno , S. ; Vinas-Bravo , O. ; Smith , S. M. ; Reyes , S. M. ; Sandoval-Ramirez , J. S. A convenient procedure for the synthesis of 3b-hydroxy-6-oxo-5a-steroids: Application to the synthesis of laxogenin . J. Braz. Chem. Soc. 2005 , 16 , 381 – 385 .
   PubMed Web of Science ®Google Scholar
• Reviews about spiroketals: (a) Vaillancourt , V. ; Pratt , N. E. ; Perron , F. ; Albizati , K. F. In The Total Synthesis of Natural Products ; John Apsimon , Ed.; John Wiley & Sons , New York , 1992 ; Vol. 8 , p. 533 ; (b) Francke , W. ; Kitching , W. Spiroacetals in insects. Curr. Org. Chem. 2001, 5 , 233 – 251 ; (c) Brimble , M. A. Radical oxidative cyclization of spiroacetals to bis-spiroacetals: An overview. Molecules 2004, 9 , 394 – 404 ; (d) Brimble , M. A. ; Furkert , D. P. Chemistry of bis-spiroacetal systems: natural products, synthesis and stereochemistry. Curr. Org. Chem. 2003, 7 , 1461 – 1484 .
   Google Scholar
• (a) Doubsky , J. ; Streinz , L. ; Saman , D. ; Zednik , J. ; Koutek , B. Alkynyltrifluoroborates as versatile tools in organic synthesis: A new route to spiroketals . Org. Lett. 2004 , 6 , 4909 ; (b) Mead , K. T. ; Brewer , B. N. Strategies in spiroketal synthesis revisited: Recent applications and advances . Curr. Org. Chem. 2003 , 7 , 227 – 256 ; (c) Tursun , A. ; Canet , I. ; Aboab , B. ; Sinibaldi , M. E. A short and versatile route to chiral spiroketal skeletons . Tetrahedron Lett. 2005 , 46 , 2291 – 2294 ; (d) Greef , M. ; Zard , S. Z. Unified, radical-based approach for the synthesis of spiroketals . Org. Lett. 2007 , 9 , 1773 – 1776 ; (e) Sommer , S. ; Kuhn , M. ; Waldmann , H. Solid-phase synthesis of [5.5]-spiroketals . Adv. Synth. Catal. 2008 , 350 , 1736 – 1750 .
   PubMed Web of Science ®Google Scholar
• (a) Yavari , I. ; Moradi , L. ; Mokhtarporyani-sanandaj , A. ; Mirzaei , A. Efficient synthesis of trialkyl 3-phenylbuta-1,3-diene-1,2,4-tricarboxylates by a novel one-pot multicomponent reaction. Helv. Chim. Acta 2007, 90, 392–394; (b) Yavari , I. ; Hossaini , Z. ; Sabbaghan , M. ; Ghazanfarpour-Darjani , M. Efficient synthesis of functionalized spiro-2,5-dihydro-1,2-λ 5 -oxaphospholes. Tetrahedron 2007, 63, 9423–9428.
   Web of Science ®Google Scholar
• (a) Engel , R. Synthesis of Carbon-Phosphorus Bonds ; CRC Press : Boca Raton , FL , 1998 ; (b) Hudson , H. R. In The Chemistry of Organophosphorus Compounds, Volume 1. Primary, Secondary and Tertiary Phosphines, Polyphosphines and Heterocyclic Organophosphorus(III) Compounds ; Hantely , F. R. , Ed.; Wiley : New York , 1990 ; pp. 386 – 472 ; (c) Johnson , A. W. Ylid Chemistry ; Academic Press : New York , 1966 .
   Google Scholar
• (a) Ferrer , P. ; Auendano , C. ; Sollhuber , M. Synthesis of 5,8-dimethoxy-2(1H)-quinolinones by intramolecular Wittig reaction . Liebigs Ann. Chem. 1995 , 1895 – 1899 ; (b) Kolodiazhynyi , O. I. Methods of preparation of C-substituted phosphorus ylides and their application in organic synthesis . Russ. Chem. Rev. 1997 , 66 , 225 – 254 ; (c) Arduago , A. J. ; Stewart , C. A. Low coordinate hypervalent phosphorus . Chem. Rev. 1994 , 94 , 1215 – 1237 .
   Google Scholar
• (a) Zbiral , E. Syntheses of heterocycles with the aid of alkylidenephosphoranes, phosphinimides, vinylphosphonium salts, and vinylphosphin-oxides . Synthesis 1974 , 775 – 797 ; (b) Becker , K. B. Cycloalkenes by intramolecular Wittig reaction . Tetrahedron 1980 , 36 , 1717 – 1745 ; (c) Bestman , H. J. ; Vostrowsky , O. Selected topics of the Wittig reaction in the synthesis of natural products . Top. Curr. Chem. 1983 , 109 , 85 – 163 .
   Google Scholar