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- Title
Biomimetic Synthesis of Meroterpenoids by Dearomatization‐Driven Polycyclization.
- Authors
Powers, Zachary; Scharf, Adam; Cheng, Andrea; Yang, Feng; Himmelbauer, Martin; Mitsuhashi, Takaaki; Barra, Lena; Taniguchi, Yoshimasa; Kikuchi, Takashi; Fujita, Makoto; Abe, Ikuro; Porco, John A.
- Abstract
A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)‐derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA‐derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA‐derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA‐derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.
- Subjects
BIOMIMETIC synthesis; BIOMIMETIC materials; SCIENTIFIC community; CHEMICAL research; BIOLOGICAL research
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 45, p16287
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201910710