Diverse Natural Products from Dichlorocyclobutanones: An Evolutionary Tale

Accounts of Chemical Research

Volumn 49, Issue 2, 2016, Pages 252-261

  Deprés, Jean Pierre ^a   Delair, Philippe ^a   Poisson, Jean François ^a   Kanazawa, Alice ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; CYCLOBUTANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; DIAZOMETHANE; GAMMA BUTYROLACTONE; PYRROLIZIDINE ALKALOID;

4-BUTYROLACTONE; CYCLOBUTANES; CYCLOPENTANES; DIAZOMETHANE; PYRROLIDINONES; PYRROLIZIDINE ALKALOIDS;

EID: 84958244396     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00493     Document Type: Article

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41. For the related preparation of ynethiol ethers, see: Nebois, P.; Kann, N.; Greene, A. E. A Simple, General Preparation of S-Alkyl and S-Aryl Ynethiol Ethers J. Org. Chem. 1995, 60, 7690-7692 10.1021/jo00128a051
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51. See also: Darses, B.; Greene, A. E.; Poisson, J.-F. Asymmetric Synthesis of Functionalized, Monocyclic Chlorocyclobutenes Org. Lett. 2010, 12, 3994-3997 10.1021/ol101559b
52. 2OTIPS-substituted cyclobutanone is particularly interesting, since it is an example of an occurrence of cycloaddition at the expense of a Claisen rearrangement (involving a 1,3-dipolar intermediate). See: Malherbe, R.; Rist, G.; Bellus, D. Reactions of Haloketenes with Allyl Ethers and Thioethers: A New Type of Claisen Rearrangement J. Org. Chem. 1983, 48, 860-869 10.1021/jo00154a023
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54. M. B. de Azevedo, M.; Murta, M. M.; Greene, A. E. Novel, Enantioselective Lactone Construction. First Synthesis of Methylenolactocin, Antitumor Antibiotic from Penicillium sp J. Org. Chem. 1992, 57, 4567-4569 10.1021/jo00043a003
55. Murta, M. M.; M. B. de Azevedo, M.; Greene, A. E. Synthesis and Absolute Stereochemistry of (-)-Protolichesterinic acid, Antitumor Antibiotic Lactone from Cetraria islandica J. Org. Chem. 1993, 58, 7537-7541 10.1021/jo00078a037
56. Tamura, Y.; Minamikawa, J.; Ikeda, M. O-Mesitylenesulfonylhydroxylamine and Related Compounds-Powerful Aminating Reagents Synthesis 1977, 1-17 10.1055/s-1977-24260
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58. Nebois, P.; Greene, A. E. Novel Enantioselective Approach to γ-Lactams from Chiral Enol Ethers: Synthesis of (-)-Statine J. Org. Chem. 1996, 61, 5210-5211 10.1021/jo961035d
59. Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. Practical Asymmetric Approach to Pyrrolidinones: Efficient Synthesis of (+)-Preussin and (-)-AHPPA J. Org. Chem. 1998, 63, 4660-4663 10.1021/jo9801162
60. Ceccon, J.; Poisson, J.-F.; Greene, A. E. Extending the Scope of the [2 + 2] Cycloaddition of Dichloroketene to Chiral Enol Ethers: Synthesis of (-)-Detoxinine Synlett 2005, 1413-1416 10.1055/s-2005-868515
61. Delair, P.; Brot, E.; Kanazawa, A.; Greene, A. E. Formal Total Synthesis of Enantiopure (-)-Anisomycin, Antibiotic from Streptomyces J. Org. Chem. 1999, 64, 1383-1386 10.1021/jo981908z
62. For a review, see: Robertson, J.; Stevens, K. Pyrrolizidine Alkaloids Nat. Prod. Rep. 2014, 31, 1721-1788 10.1039/C4NP00055B
63. For a review, see: Michael, J. P. Indolizidine and Quinolizidine Alkaloids Nat. Prod. Rep. 2008, 25, 139-165 10.1039/B612166G
64. Roche, C.; Kadlecikova, K.; Veyron, A.; Delair, P.; Philouze, C.; Greene, A. E.; Flot, D.; Burghammer, M. New Asymmetric Approach to Natural Pyrrolizidines: Synthesis of (+)-Amphorogynine A, (+)-Amphorogynine D, and (+)-Retronecine J. Org. Chem. 2005, 70, 8352-8363 10.1021/jo050983o
65. 2 Tetrahedron: Asymmetry 2015, 26, 85-94 10.1016/j.tetasy.2014.12.002
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67. 2 J. Org. Chem. 2013, 78, 4840-4849 10.1021/jo400386f
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70. Ceccon, J.; Greene, A. E.; Poisson, J.-F. Asymmetric [2 + 2] Cycloaddition: Total Synthesis of (-)-Swainsonine and (+)-6-Epicastanospermine Org. Lett. 2006, 8, 4739-4742 10.1021/ol0617751
71. Ceccon, J.; Danoun, G.; Greene, A. E.; Poisson, J.-F. Asymmetric Synthesis of (+)-Castanospermine Through Enol Ether Metathesis-Hydroboration/Oxidation Org. Biomol. Chem. 2009, 7, 2029-2031 10.1039/b901488h
72. This strategy has also been used in an efficient synthesis of (+)-1-deoxynojirimycin. See: Danoun, G.; Ceccon, J.; Greene, A. E.; Poisson, J.-F. Stereocontrolled Total Synthesis of (+)-1-Deoxynojirimycin Eur. J. Org. Chem. 2009, 2009, 4221-4224 10.1002/ejoc.200900595
73. Kamath, A.; Fabritius, C.-H.; Philouze, C.; Delair, P. A New Approach to the 8b-Azaacenaphthylene Ring System Org. Biomol. Chem. 2015, 13, 9834-9843 10.1039/C5OB01013F