Asymmetric total synthesis of (-)-panacene and correction of its relative configuration

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3597-3599

  Boukouvalas, John ^a   Pouliot, Martin ^a   Robichaud, Joël ^a,c   MacNeil, Stephen ^b,d   Snieckus, Victor ^b  

^a UNIVERSITÉ LAVAL   (Canada)

^b QUEEN S UNIVERSITY   (Canada)

^c MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^d WILFRID LAURIER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BROMINATED HYDROCARBON; PALLADIUM; PANACENE;

ANIMAL; APLYSIA; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; ANIMALS; APLYSIA; CATALYSIS; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 33747275056     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061385e     Document Type: Article

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43. Feldman's assignment of the relative stereochemistry of panacene as 1 is based primarily on the appearance of the C3-H (triplet rather than dd), although it is mentioned (ref 5a) that the chemical shift of C3-H in (±)-2 (δ 5.46), but not (±)-1 (δ 5.50), is identical with that of panacene (δ 5.46). The appearance of this peak can indeed be misleading since it depends on shimming. We found that this proton often appears like a triplet in both isomers at 300 and 400 MHz. In addition, we have observed that the two isomers can also be distinguished by the Δδ of C5-α-H. Once again, it is ent-2 (δ 2.48), and not 1 (δ 2.46), that is a perfect match for panacene (δ 2.48, ref 1).
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