Total synthesis of resveratrol-based natural products: A chemoselective solution

Angewandte Chemie - International Edition

Volumn 46, Issue 43, 2007, Pages 8186-8191

  Snyder, Scott A ^a   Zografos, Alexandros L ^a   Lin, Yunqing ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Chemoselectivity; Natural products; Resveratrol; Total synthesis

Indexed keywords

BIOACTIVITY; OLIGOMERS; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVITY; NATURAL PRODUCTS; RESVERATROL;

SOLUTIONS;

BIOLOGICAL PRODUCT; RESVERATROL; STILBENE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

BIOLOGICAL PRODUCTS; STILBENES;

EID: 36048988677     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703333     Document Type: Article

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48. All evidence indicates that the aryl group has not shifted within 33. Although this compound has proven too difficult to obtain in a pure enough form to verify its connectivity through NOE experiments (owing to its sensitivity), we have substituted the acetate within structure 36 for chloride with retention of configuration. This compound, along with 36 and 37, possess the four aryl protons of the 3,5-dimethoxybenzene rings tightly and consistently grouped between a = 6.40 and 6.90 ppm; by contrast, bromide 33 possesses one of these signals as an outlier at δ = 5.76 ppm, presumably the one that is in close proximity to the halogen atom.
49. In all cases, spectral data for synthetic materials perfectly match those of the natural isolates. It should be noted that all molecules reported in this manuscript are racemic.