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Two-phase synthesis of (-)-taxuyunnanine D

Journal of the American Chemical Society, ISSN: 1520-5126, Vol: 136, Issue: 13, Page: 4909-4912
2014
  • 91
    Citations
  • 0
    Usage
  • 183
    Captures
  • 3
    Mentions
  • 14
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    91
  • Captures
    183
  • Mentions
    3
    • Blog Mentions
      2
      • Blog
        2
    • References
      1
      • Wikipedia
        1
  • Social Media
    14
    • Shares, Likes & Comments
      14
      • Facebook
        14

Most Recent Blog

Academia–industry collaboration in the route optimization of taxadienone

Reaction scale-up: We made ~2 g of taxadienone whereas AMRI made ~10 g. Reaction yields: Please see the figure below. Our laboratory is engaged in many collaborations with industrial groups, including LEO Pharma, Bristol-Myers Squibb, and Sigma-Aldrich, and in most cases, our industrial partner has a project goal toward which we provide expertise and in-house research findings.

Article Description

The first successful effort to replicate the beginning of the Taxol oxidase phase in the laboratory is reported, culminating in the total synthesis of taxuyunnanine D, itself a natural product. Through a combination of computational modeling, reagent screening, and oxidation sequence analysis, the first three of eight C-H oxidations (at the allylic sites corresponding to C-5, C-10, and C-13) required to reach Taxol from taxadiene were accomplished. This work lays a foundation for an eventual total synthesis of Taxol capable of delivering not only the natural product but also analogs inaccessible via bioengineering. © 2014 American Chemical Society.

Bibliographic Details

Wilde, Nathan C; Isomura, Minetaka; Mendoza, Abraham; Baran, Phil S

American Chemical Society (ACS)

Chemical Engineering; Chemistry; Biochemistry, Genetics and Molecular Biology

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