Total synthesis of (-)-cylindrocyclophane a via a double Horner-Emmons macrocyclic dimerization event [2]

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4982-4983

  Hoye, Thomas R ^a   Humpai, Paul E ^a   Moon, Bongjin ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYLINDROCYCLOPHANE A; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

CYCLIZATION; DIMERIZATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034709454     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000429q     Document Type: Letter

References (26)

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11. Successful relevant macrocyclic dimerization reactions were reported (a) Hoye, T. R., Humpal, P. E. Presented at the 212th National Meeting of the American Chemical Society, Orlando, FL, August 1996; paper ORGN 173. (b) Humpal, P. E. Ph.D. Thesis, University of Minnesota, 1996.
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16. 1H NMR analysis of the sec-phenethyl ester 12 and confirmed at the stage of primary alcohol 13 by analysis of its Mosher ester. The absolute configuration of the new benzylic stereocenter was assumed to be R based upon a chair-transition state for the Claisen rearrangement.
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26. 3/EtSH, conditions that were not successful in the case of conversion of 29 to 1A.