Total synthesis of elaiolide using a copper(l)-promoted stille cyclodimerization reaction

Organic Letters

Volumn 1, Issue 1, 1999, Pages 19-22

  Paterson, Ian ^a   Lombart, Henry Georges ^a   Allerton, Charlotte ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000274038     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990004c     Document Type: Article

References (57)

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39. 9 is protected prevents direct esterification, and an esterification on the diol 15 is thus required.
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44. 1H NMR of the crude reaction mixture.
45. 7-OH.
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51. The structures of these macrocycles were confirmed by FAB MS.
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54. 3 etherate. These conditions (Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed., in press) provided a 7:1 ratio in favor of the desired aldol in model studies, producing hemiacetal 19 on deprotection. In contrast, with diketone 17 only recovered starting ketone and aldehyde were isolated. (equation presented)
55. Using TASF, only 35% of elaiolide was obtained, accompanied by an eliminated compound which was also formed in the degradation of elaiophylin: Scheldt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, C. D.; Roush, W. R. J. Org. Chem. 1998, 63, 6436.
56. 5
57. 13C NMR data for elaiolide with comparative data previously reported.