4.8 Article

Total Synthesis of (±)-Grandilodine B

Journal

ORGANIC LETTERS
Volume 19, Issue 7, Pages 1828-1830

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00591

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Funding

  1. Tsinghua University
  2. 1000 Talents Recruitment Program
  3. National Natural Science Foundation of China [21672123]

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The first total synthesis of the opened-type Kopsia alkaloid grandilodine B is reported. Four stereocenters of this alkaloid, three of them quaternary, are stereoselectively generated by a Diels-Alder reaction, a diastereoselective cyanation of tertiary alcohol, and a facial selective nitrone 1,3-dipolar cycloaddition.

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