Enantiocontrolled Construction of Functionalized Tetrahydrofurans: Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1414-1418

  Wang, Zhi Min ^a   Shen, Ming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001727935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971324h     Document Type: Article

References (48)

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45. The ds value of 17 was determined by GC-MS on OV-1 column.
46. 4.
47. The two isomers were separated by chromatography on silica gel column. Their ratio was then determined by their weights.
48. 13C NMR of our synthetic sample to those in refs 11 and 12 verified that the major isomer we obtained was the 10R natural product. The diagnostic NMR chemical shift of different THF subunits with various relative configurations in Annonaceous acetogenins showed that when the relative configuration of the THF ring and adjacent OH group was threo, the range of the chemical shift of the proton on the carbon with adjacent OH group was 3.34-3.41 ppm, and for the erythro isomer, the range of chemical shift was 3.80-3.90 ppm. For our synthetic sample, the chemical shift was 3.37 ppm, which was in accordance with the threo configuration. This observation further confirmed our identification. Equation Presented