Journal
SYNLETT
Volume 33, Issue 11, Pages 1087-1091Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1828-0352
Keywords
lusianthridin; dihydrophenanthrene; Suzuki-Miyaura reaction; intramolecular nucleophilic substitution; large-scale preparation of stilbenoids
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Funding
- National Natural Science Foundation of China [22001172, 22071155, 21871184]
- Shanghai Municipal Education Commission [2019-01-07-00-10-E00072]
- Shanghai Sailing Program [20YF1449300]
- Chenguang Program [20CG52]
- Program of Shanghai Academic/Technology Research Leader [20XD1403600]
- Science and Technology Commission of Shanghai Municipality [20400750300]
- Innovation Team and Talents Cultivation Program of the National Administration of Traditional Chinese Medicine [ZYYCXTD-202004]
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An efficient synthesis of the stilbenoid lusianthridin is described, wherein a Suzuki-Miyaura coupling and an intramolecular nucleophilic substitution are employed as key reactions to construct the 9,10-dihydrophenanthrene core. The synthesis is accomplished in seven steps with a 13.2% overall yield, and each step can be conducted on a >20 gram scale. This route has provided 20 grams of lusianthridin for further biological activity studies.
The efficient preparation of the stilbenoid lusianthridin is described. This synthesis relies on a Suzuki-Miyaura coupling and an intramolecular nucleophilic substitution as key reactions to construct the 9,10-dihydrophenanthrene core. The synthesis is completed in seven steps with a 13.2% overall yield, and each step can be conducted on a >20 gram scale. The route has provided 20 grams of lusianthridin for further biological activity studies.
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