Acid-catalyzed synthesis of bicyclo[3. n.1]alkenediones

Organic Letters

Volumn 13, Issue 4, 2011, Pages 664-667

  Michaelides, Iacovos N ^a   Darses, Benjamin ^a   Dixon, Darren J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BIOLOGICAL PRODUCT; CATECHIN; DRUG DERIVATIVE; KETONE; VITISINOL D;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS; BIOLOGICAL PRODUCTS; CATALYSIS; CATECHIN; KETONES; STEREOISOMERISM;

EID: 79951622667     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102909t     Document Type: Article

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31. ]. The crystal structure of 10a was solved using SIR92 [ Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435 ]
32. and refined using the CRYSTALS software suite [ Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487 ], as per the Supporting Information (CIF).
33. Since TBAF was described as a basic promoting agent for this type of reaction (ref 8) TsOH was also replaced by TBAF, but only decomposition of the starting material was observed in this case.
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35. However, the 9-membered cyclization substrate proved to be unreactive under TsOH catalysis, and no product was observed.
36. For the preparation of 9j from 9e, see the Supporting Information.