The brosimum allene: A structural revision

Organic Letters

Volumn 10, Issue 23, 2008, Pages 5493-5496

  Hu, Gaojie ^a   Liu, Kai ^a   Williams, Lawrence J ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; SOLVENT; PROPADIENE;

ARTICLE; CHEMISTRY; MORACEAE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKADIENES; MAGNETIC RESONANCE SPECTROSCOPY; MORACEAE; SOLVENTS;

EID: 61349137576     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802338z     Document Type: Article

References (50)

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23. All structures were fully optimized by analytical gradient methods using the Gaussian 03 suites: (a) Frisch, M. J.; Trucks, G. W.; Schlege, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004 (see the Supporting Information for the full citation.)
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28. 13C NMR signals for A.
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32. There is a strong analogy between this proposal and quinonemethide- forming eliminations, see for example ref 13. Moreover, oxidative conversion of 10 (LG = H) to 11 represents another potential route to this moiety.
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34. Potter, G. A.; McCague, R. J. Org. Chem. 1990, 55, 6184 The major byproduct of this reaction (50%) is the adduct derived from THF and then N-phenyltrifluoromethanesulfonamide addition to the TBS oxocarbenium analogue of 8 (see the Supporting Informationfor details and characterization of this substance). The use of ether as solvent for this reaction proved ineffective and gave 14 in 4% isolated yield.
35. The quality of the DMF was found to be important, as old DMF gave 17 directly (35-50%).
36. These observations do not speak to issues of biosynthesis and do not preclude analogous oxidative transformations (see ref 14).
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50. Understandably, structural misassignments, despite our many modern advantages, are not uncommon: Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 6012.