The Michael T. Crimmins Group Home Page

• 2005-2009
• 2000-2004
• 1995-1999
• 1990-1994
• 1985-1989
• 1983-1984
• YEARS:

• [2 + 2]
• Spiroketals
• Aldol/RCM
• Ginkgolide
• Brevetoxin
• Eunicellins
• Syntheses
• PROJECTS:

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Methodology

94. "Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries" Crimmins, M. T.; Shamszad, M. J. Org. Chem. 2007, 9, 149-152.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol062688b |

77. "An Improved Procedure For Asymmetric Aldol Additions With N-Acyl Oxazolidinones, Oxazolidinethiones, and Thiazolidinethiones" Crimmins, M. T.; She, J. Synlett 2004, 8, 1371-1374.
| Full Article-PDF | DOI: 10.1055/s-2004-825626 |

71. "Anti-Selective Aldol Reactions with Titanium Enolates of N-Glycolyloxazolidinethiones" Crimmins, M. T.; McDougall, P. J. Org. Lett. 2003, 5, 591-594.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol034001i |

62. "Asymmetric Aldol Additions: Use of Titanium Tetrachloride and (-)-Sparteine for the Soft Enolization of N-Acyl Oxazolidinones, Oxazolidinethiones, and Thiazolidinethiones" Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/jo001387r |

61. "An Efficient, General Asymmetric Synthesis of Carbocyclic Nucleosides: Application of an Asymmetric Aldol/Ring-Closing Metathesis Strategy" Crimmins, M. T.; King, B. W.; Zuercher, W. J.; Choy, A. L. J. Org. Chem. 2000, 65, 8499-8509.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/jo005535p |

59. "Diastereoselective Alkylations of Oxazolidinone Glycolates: A Useful Extension of the Evans Asymmetric Alkylation" Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165-2167.
| Full Article-PDF | DOI: 10.1021/ol006091m |

58. "An Efficient Strategy for the Synthesis of α,α'-cis and trans-Disubstituted Medium Ring Ethers" Crimmins, M. T.; Emmitte, K. A. Synthesis 2000, 6, 899-903.
| Full Article-PDF | DOI: 10.1055/s-2000-6268 |

56. "Solid-Phase Synthesis of Carbocyclic Nucleosides" Crimmins, M. T.; Zuercher, W. J. Org. Lett. 2000, 2, 1065-1067.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol005614n |

54. "Titanium Enolates of Thiazolidinethione Chiral Auxiliaries: Versatile Tools for Asymmetric Aldol Additions" Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775-777.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol9913901 |

49. "An Asymmetric Aldol-Ring-Closing Metathesis Strategy for the Enantioselective Construction of Oxygen Heterocycles: An Efficient Approach to the Enantioselective Synthesis of (+)-Laurencin" Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja990421k |

39. "An Asymmetric Aldol - Ring Closing Metathesis Strategy for the Enantioselective Construction of Six to Nine Membered Oxygen Heterocycles" Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/jo9716688 |

37. "Asymmetric Aldol Additions with Titanium Enolates of Acyloxazolidinethiones: Dependence of Selectivity on Amine Base and Lewis Acid Stoichiometry" Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-7884.
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja9716721 |

Examples in Synthesis

104. "A Highly Convergent Approach toward (-)-Brevenal" Crimmins, M. T.; Shamszad, M.; Mattson, A. E. Org. Lett. 2010, 12, 2614-2617.
• Syn Aldol • Glycolate Alkylation
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol1008203 |

103. "Total Synthesis of Irciniastatin A (Psymberin)" Crimmins, M. T.; Stevens, J. M.; Schaaf, G. M. Org. Lett. 2009, 11, 3990-3993.
• Anti Glycolate Aldol • Syn Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol901655e |

101. "Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits" Crimmins, M. T.; Ellis, J. M.; Emmitte, K. A.; Haile, P. A.; McDougall, P. J.; Parrish, J. D.; Zuccarello, J. L. Chem. Eur. J. 2009, 15, 9223-9234.
• Glycolate Alkylation/RCM • Syn Glycolate Aldol/RCM • Anti Glycolate Aldol/RCM • Syn Aldol/RCM • Acetate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1002/chem.200900776 |

100. "Asymmetric Total Synthesis of Pyranicin" Crimmins, M. T.; Jacobs, D. L. Org. Lett. 2009, 11, 2695-2698.
• Syn Glycolate Aldol/RCM • Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol900814w |

99. "Enantioselective Total Synthesis of (-)-Pironetin: Iterative Aldol Reactions of Thiazolidinethiones" Crimmins, M. T.; Dechert, A.-M. R. Org. Lett. 2009, 11, 1635-1638.
• Syn Aldol • Acetate Aldol • Acetal Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol9003228 |

95. "An Intramolecular Diels-Alder Strategy for the Asbestinins: Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12" Crimmins, M. T.; Ellis, J. M. J. Org. Chem. 2008, 73, 1649-1660.
• Syn Glycolate Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/jo0712695 |

93. "Synthesis of the C29-C37 Bicyclic Ether Core of (+)-Sorangicin A" Crimmins, M. T.; Haley, M. W. Org. Lett. 2006, 8, 4223-4225.
• Anti Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol061339e |

92. "Improved Synthesis of the ABCDE Fragment of Brevetoxin A" Crimmins, M. T.; McDougall, P. J.; Ellis, J. M. Org. Lett. 2006, 8, 4079-4082.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol0615782 |

91. "Enantioselective Total Synthesis of (+)-SCH 351448" Crimmins, M. T.; Vanier, G. S. Org. Lett. 2006, 8, 2887-2890.
• Syn Aldol • Glycolate Alkylation/RCM • Acetate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol061073b |

90. "Total Synthesis of (-)-Mucocin" Crimmins, M. T.; Zhang, Y.; Diaz, F. A. Org. Lett. 2006, 8, 2369-2372.
• Syn Glycolate Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol060704z |

89. "Formal Synthesis of 6-Deoxyerythronolide B" Crimmins, M. T.; Slade, D. J. Org. Lett. 2006, 8, 2191-2194.
• Syn Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol0607241 |

88. "Enantioselective Total Synthesis of Bistramide A" Crimmins, M. T.; DeBaillie, A. C. J. Am. Chem. Soc. 2006, 128, 4936-4937.
• Syn Aldol • Glycolate Alkylation
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja057686l |

87. "Enantioselective Total Synthesis of FD-891" Crimmins, M. T.; Caussanel, F. J. Am. Chem. Soc. 2006, 128, 3128-3129.
• Syn Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja060018v |

85. "An Intramolecular Diels-Alder Approach to the Eunicellins: Enantioselective Total Syntheses of Ophirin B and Astrogorgin" Crimmins, M. T.; Brown, B. H.; Plake, H. R. J. Am. Chem. Soc. 2006, 128, 1371-1378.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja056334b |

84. "Convergent, Stereoselective Synthesis of the GHIJ Fragment of Brevetoxin A" Crimmins, M. T.; Zuccarello, J. L.; Cleary, P. A.; Parrish, J. D. Org. Lett. 2006, 8, 159-162.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol0526625 |

83. "Establishing the Absolute Configuration of the Asbestinins: Enantioselective Total Synthesis of 11-Acetoxy-4-deoxyasbestinin D" Crimmins, M. T.; Ellis, J. M. J. Am. Chem. Soc. 2005, 127, 17200-17201.
• Syn Glycolate Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja056921x |

82. "Enantioselective Synthesis of Apoptolidinone: Exploiting the Versatility of Thiazolidinethione Chiral Auxiliaries" Crimmins, M. T.; Christie, H. S.; Chaudhary, K.; Long, A. J. Am. Chem. Soc. 2005, 127, 13810-13812.
• Glycolate Alkylation • Syn Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja0549289 |

81. "Enantioselective Synthesis of Apoptolidin Sugars" Crimmins, M. T.; Long, A. Org. Lett. 2005, 7, 4157-4160.
• Anti Glycolate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol0515107 |

80. "A Convergent Coupling Strategy for the Formation of Polycyclic Ethers: Stereoselective Synthesis of the BCDE Fragment of Brevetoxin A" Crimmins, M. T.; McDougall, P. J.; Emmitte, K. A. Org. Lett. 2005, 7, 4033-4036.
• Anti Glycolate Aldol • Glycolate Alkylation/RCM • Syn Aldol • Anti Glycolate Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol051543m |

79. "Enantioselective Total Synthesis of (+)-Gigantecin: Exploiting the Asymmetric Glycolate Aldol Reaction" Crimmins, M. T.; She, J. J. Am. Chem. Soc. 2004, 126, 12790-12791.
• Glycolate Alkylation/RCM • Syn Glycolate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja0455852 |

78. "An Intramolecular Diels-Alder Approach to the Eunicelins: Enantioselective Total Synthesis of Ophirin B" Crimmins, M. T.; Brown, B. H. J. Am. Chem. Soc. 2004, 126, 10264-10266.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja046574b |

74. "Enantioselective Total Synthesis of (+)-Leucascandrolide A Macrolactone" Crimmins, M. T.; Siliphaivanh, P. Org. Lett. 2003, 5, 4641-4644.
• Acetate Aldol • Glycolate Alkylation
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol035797o |

73. "Enantioselective Total Synthesis of (+)-Rogioloxepane A" Crimmins, M. T.; DeBaillie, A. C. Org. Lett. 2003, 5, 3009-3011.
• Glycolate Alkylation/RCM • Acetate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol034923l |

72. "Enantioselective Total Synthesis of (+)-Obtusenyne" Crimmins, M. T.; Powell, M. T. J. Am. Chem. Soc. 2003, 125, 7592-7595.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja029956v |

70. "Asymmetric Total Synthesis of (-)-Laulimalide: Exploiting the Asymmetric Glycolate Alkylation Reaction" Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958-5959.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja026269v |

68. "Ring Closing Metathesis for the Formation of Medium Ring Ethers: The Total Synthesis of (-)-Isolaurallene" Crimmins, M. T.; Emmitte, K. A.; Choy, A. L. Tetrahedron 2002, 58, 1817-1834.
• Syn Glycolate Aldol/RCM • Glycolate Alkylation/RCM
| Full Article-PDF | DOI: 10.1016/S0040-4020(02)00040-6 |

65. "Formal Total Synthesis of (+)-Trehazolin. Application of an Asymmetric Aldol-Olefin Metathesis Approach to the Synthesis of Functionalized Cyclopentenes" Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012-4018.
• Syn Aldol/RCM
| Full Article-PDF | DOI: 10.1021/jo015568k |

64. "An Aldol Approach to the Synthesis of the EF Fragment of Spongistatin 1" Crimmins, M. T.; Katz, J. D.; McAtee, L. C.; Tabet, E. A.; Kirincich, S. J. Org. Lett. 2001, 3, 949-952.
• Syn Aldol • Syn Glycolate Aldol • Glycolate Alkylation
| Full Article-PDF | DOI: 10.1021/ol015652m |

63. "Asymmetric Total Synthesis of (-)-Isolaurallene" Crimmins, M. T.; Emmitte, K. A. J. Am. Chem. Soc. 2001, 123, 1533-1534.
• Glycolate Alkylation/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja005892h |

57. "Total Synthesis of (+)-Prelaureatin and (+)-Laurallene" Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473-5476.
• Syn Glycolate Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja0007197 |

53. "Synthesis of the C1-C13 Fragment of Leucascandrolide A" Crimmins, M. T.; Carroll, C. A.; King, B. W. Org. Lett. 2000, 2, 597-599.
• Alkylation
| Full Article-PDF | DOI: 10.1021/ol991345t |

48. "Total Synthesis of (+)-Laurencin: An Asymmetric Alkylation-Ring-Closing Metathesis Approach to Medium Ring Ethers" Crimmins, M. T.; Emmitte, K. A. Org. Lett. 1999, 1, 2029-2032.
• Glycolate Alkylation/RCM • Acetate Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ol991201e |

47. "Asymmetric Total Synthesis of Callystatin A: Asymmetric Aldol Additions with Titanium Enolates of Acyloxazolidinethiones" Crimmins, M. T.; King, B. W. J. Am. Chem. Soc. 1998, 120, 9084-9085.
• Syn Aldol
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/ja9817500 |

35. "An Efficient Asymmetric Approach to Carbocyclic Nucleosides: Asymmetric Synthesis of 1592U89, a Potent Inhibitor of HIV Reverse Transcriptase" Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193.
• Syn Aldol/RCM
| Full Article-PDF | (Supporting Information) | DOI: 10.1021/jo960708p |