4.8 Article

Asymmetric Total Synthesis of PD-116740

Journal

ORGANIC LETTERS
Volume 23, Issue 2, Pages 469-473

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03990

Keywords

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Funding

  1. National Natural Science Foundation of China [21971068, 21772044]
  2. Program of Shanghai Academic/Technology Research Leader [18XD1401500]
  3. Program of Shanghai Science and Technology Committee [18JC1411303]
  4. Shuguang Program - Shanghai Education Development Foundation [19SG21]
  5. Program for Changjiang Scholars and Innovative Research Team in University
  6. Fundamental Research Funds for the Central Universities
  7. National Young Top-Notch Talent Support Program

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A new approach was developed for the asymmetric total synthesis of (+)-PD-116740, involving a sequence of asymmetric dihydroxylation followed by oxidative cyclization. A new Cu salt was found to be the best oxidant for inducing the oxidative coupling and phenol oxidation, providing a valuable strategy for future pharmaceutical research.
A new approach was developed to achieve the asymmetric total synthesis of (+)-PD-116740, an angucyclinone from the actinomycete isolate (WP 4669). A sequence of asymmetric dihydroxylation followed by oxidative cyclization was applied to stereoselectively construct the core trans-9,10-dihydrophenanthrene-9,10-diol B-C-D ring. A new Cu salt Cu(OH)OTf center dot NMI2 was found to be the best oxidant to induce the oxidative coupling and phenol oxidation.

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