Synlett 2012; 23(10): 1489-1492
DOI: 10.1055/s-0031-1290670
letter
© Georg Thieme Verlag Stuttgart · New York

A Modular, Stereoselective Approach to Spiroketal Synthesis

Michael T. Crimmins*
,
Adam M. Azman
Weitere Informationen

Publikationsverlauf

Received: 10. Februar 2012

Accepted after revision: 30. März 2012

Publikationsdatum:
29. Mai 2012 (online)


Abstract

A highly convergent and flexible synthetic approach to stereochemically defined spiroketals is reported. Substituents can be incorporated at various positions around the spiroketal framework without significant disruption to the synthetic scheme. The approach has been exploited to prepare the spiroketal fragment of milbemycin β14.

Supporting Information

 
  • References

  • 1 Current Address: Butler University, Indianapolis, IN, USA
  • 2 Perron F, Albizati KF. Chem. Rev. 1989; 89: 1617
    • 3a Francke W, Heeman V, Gerken B, Renwick JA. A, Vite JP. Naturwissenschaften 1977; 64: 590
    • 3b Dettner K, Schwinger G. Z. Naturforsch., C: Biosci. 1986; 41: 366
    • 3c Vite JP, Francke W. Naturwissenschaften 1976; 63: 550
  • 4 Yeung K.-S, Paterson I. Chem. Rev. 2005; 105: 4237
  • 5 Aho JE, Pihko PM, Rissa TK. Chem. Rev. 2005; 105: 4406
    • 6a Juaristi E, Cuevas G. Tetrahedron 1992; 48: 5019
    • 6b Juaristi E, Cuevas G. The Anomeric Effect . 1st ed. CRC Press; Boca Raton, FL: 1994
    • 6c Lemieux R, Pavia A. Can. J. Chem. 1969; 47: 4441
    • 6d Deslongchamps P, Rowan DD, Pothier N, Sauve T, Saunders JK. Can. J. Chem. 1981; 59: 1122
    • 7a Crimmins MT, King BW, Tabet EA, Chaudhary K. J. Org. Chem. 2001; 66: 894
    • 7b Crimmins MT, Shamszad M. Org. Lett. 2007; 9: 149
  • 8 Evans DA, Downey CW, Shaw JT, Tedrow JS. Org. Lett. 2002; 4: 1127
  • 9 Marshall JA, Chen M. J. Org. Chem. 1997; 62: 5996
    • 10a Crimmins MT, Kirincich SJ, Wells AJ, Choy AL. Synth. Commun. 1998; 28: 3675
    • 10b Crimmins MT, Choy AL. J. Am. Chem. Soc. 1999; 121: 5653
  • 11 Paterson I, Yeung K, Smaill JB. Synlett 1993; 774
  • 12 Tsuda T, Hayashi T, Satomi H, Kawamoto T, Saegusa T. J. Org. Chem. 1986; 51: 537
  • 13 Crimmins MT, O’Bryan EA. Org. Lett. 2010; 12: 4416
  • 14 Xiang W, Wang J, Fan H, Wang X, Zhang J. J. Antibiot. 2008; 61: 27
    • 15a Northrup AB, MacMillan DW. C. J. Am. Chem. Soc. 2002; 124: 6798
    • 15b Crossman JS, Perkins MV. J. Org. Chem. 2006; 71: 117
    • 15c Wilkinson AL, Hanefeld U, Wilkinson B, Leadlay PF, Staunton J. Tetrahedron Lett. 1998; 39: 9827