Novel asymmetric route to carbanucleoside and prostanoid intermediates: Efficient preparation of both optical antipodes of chiral cyclopentenone

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3806-3807

  Lin, Chun Chieh ^a   Wang, Ying Chuan ^a   Hsu, Jung Lang ^a   Chiang, Chao Cheng ^a   Su, Dah Wei ^a   Yan, Tu Hsin ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030747528     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970616f     Document Type: Article

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47. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.
48. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.
49. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.
50. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.
51. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.
52. For examples of the requirement of a proximal phenyl ring for highly diastereoselective reactions, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595. (b) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586. (c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (d) Smith, A. B.; Liverton, N. J.; Hrib, N. J.; Sivaramakrishnan, H.; Winzenberg, K. J. Am. Chem. Soc. 1986, 108, 3040. (e) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (f) Whitesell. J. K. Acc. Chem. Soc. 1985, 18, 280. (g) Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181.