Toward the development of a general chiral auxiliary. A remarkable, highly diastereoselective, auxiliary-mediated substitution: Application to an enantioselective synthesis of the cyclohexene subunit of (+)-tetronolide

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7238-7239

  Boeckman Jr , Robert K ^a   Wrobleski, Stephen T ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ANTIBIOTIC AGENT; TETRONOLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE; X RAY ANALYSIS;

EID: 0029856313     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961585b     Document Type: Article

References (26)

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10. Total synthesis of tetronolide: (a) Takeda, T.; Kawanishi, E.; Nakamura, H.; Yoshii, E. Tetrahedron Lett. 1991, 32, 4925. (b) Takeda, K.; Urahata, M.; Yoshii, E.; Takayanagi, H.; Oqura, H. J. Org. Chem. 1986, 51, 4735. Takeda, K.; Kobayashi, T.; Saito, K.; Yoshii, E. J. Org. Chem. 1988, 53, 1092.
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25. Owing to the sensitivity of the dibromide 6, handling is minimized. The methylene chloride solution of 6 is filtered and partially concentrated prior to direct addition to the coupling reaction. Dibromide 6 was found to rapidly epimerize upon concentration to a neat liquid. Care is taken to avoid exposure of the solution of 6 to moisture as traces of HBr apparently catalyze rapid equilibration of 6.
26. The details of the single-crystal X-ray analysis of carbamate 14 will be published as part of a full account of these studies.