期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 10, 页码 5512-5518出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202013881
关键词
cis-decalin; hydrogen atom transfer; radical cyclization; steroids; total synthesis
资金
- National Program on Key Research Project [2016YFA0602900]
- Guangdong Province Science Foundation [2017B090903003]
- Science and Technology Program of Guangzhou [201707010073]
- National Natural Science Foundation of China [21672073, 21871098]
- Fundamental Research Funds for the Central Universities, SCUT
The study demonstrates the assembly of the cis-decalin framework through radical cyclization initiated by metal-catalyzed hydrogen atom transfer (MHAT), and its application in asymmetric synthesis of target compounds. The MHAT-based approach allows for position-selective C-H oxygenation and interconversion between different natural products through radical rearrangement and biomimetic reactions.
We describe herein the assembly of the cis-decalin framework through radical cyclization initiated by metal-catalyzed hydrogen atom transfer (MHAT), further applied it in the asymmetric synthesis of dankasterones A and B and periconiastone A. Position-selective C-H oxygenation allowed for installation of the necessary functionality. A radical rearrangement was adopted to create 13(14 -> 8)abeo-8-ergostane skeleton. Interconversion of dankasterone B and periconiastone A was realized through biomimetic intramolecular aldol and retro-aldol reactions. The MHAT-based approach, serves as a new dissection means, is complementary to the conventional ways to establish cis-decalin framework.
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