2. Academic Validation
  3. Biomimetic syntheses of rubialatins A, B and related congeners

Biomimetic syntheses of rubialatins A, B and related congeners

  • Org Lett. 2015 Mar 20;17(6):1441-4. doi: 10.1021/acs.orglett.5b00321.
Hongzhi Yang,  Juan Feng,  Yuanhe Li,  Yefeng Tang 1 2
Affiliations

Affiliations

  • 1 ‡Collaborative Innovation Center for Biotherapy, Tsinghua University, Beijing 100084, China.
  • 2 §Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China.
PMID: 25723050 DOI: 10.1021/acs.orglett.5b00321
Abstract

The first total syntheses of rubialatins A and B, two newly discovered naphthohydroquinone dimers, were achieved with high efficiency and elegancy through rationally designed biomimetic approaches. The tandem ring contraction/Michael addition/aldol reaction followed by oxidation enabled the rapid access of prerubialatin from readily available precursors, which then diverted into rubialatins A and B via epoxidation and photoinduced skeletal rearrangement, respectively. Moreover, several new rubialatin congeners were also obtained along the synthetic tour, some of which were proved to be authentic Natural Products.

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