4.7 Article

Formal total synthesis of dankasterone B

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 15, Pages 3961-3965

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00299j

Keywords

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Funding

  1. National Natural Science Foundation of China [22071064, 21871098, 21672073]
  2. National Program on Key Research Project [2016YFA0602900]
  3. SCUT

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An efficient and enantioselective synthesis of an architecturally unusual ergostane-type steroid, dankasterone B, is described. The cis-decalin skeleton of the steroid is established through an intramolecular metal-catalyzed hydrogen atom transfer (MHAT) reaction, while the 13(14 -> 8)abeo-ergostane skeleton is constructed via a radical rearrangement.
An efficient and enantioselective route toward an architecturally unusual ergostane-type steroid, dankasterone B, is presented. The cis-decalin skeleton of the steroid was established by an intramolecular metal-catalyzed hydrogen atom transfer (MHAT) reaction. A radical rearrangement was used to construct the 13(14 -> 8)abeo-ergostane skeleton.

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