4.8 Article

Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain

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ORGANIC LETTERS
卷 14, 期 1, 页码 114-117

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AMER CHEMICAL SOC
DOI: 10.1021/ol202895u

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资金

  1. Naito Foundation
  2. Nagase Science and Technology Foundation
  3. Suntory Institute for Bioorganic Research
  4. Global COE from MEXT
  5. Japan Society for Promotion of Science-Asian Core Program (JSPS-ACP) on Cutting-Edge Organic Chemistry in Asia
  6. National Research Council of Thailand (NRCT)
  7. Chulabhorn Research Institute (CRI)
  8. Grants-in-Aid for Scientific Research [24580161, 20380067, 22780102] Funding Source: KAKEN

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Two possible diastereomers of the indole moiety of sespendole were synthesized from 3-hydroxy-4-nitrobenzaldehyde in a highly stereoselective manner. Comparison of H-1 and C-13 NMR spectra of the two synthetic materials with those sespendole leads us to propose that the relative stereochemistry of the epoxyalcohol is syn.

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