Asymmetric Synthesis of (−)-Aurantioclavine via Palladium-Catalyzed Intramolecular Allylic Amination
S Suetsugu, H Nishiguchi, C Tsukano…
Index: Suetsugu, Satoshi; Nishiguchi, Hiromi; Tsukano, Chihiro; Takemoto, Yoshiji Organic Letters, 2014 , vol. 16, # 3 p. 996 - 999
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Citation Number: 15
Abstract
The total synthesis of (−)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing ap-tosylamide group. The reaction using tris (dibenzylideneacetone) dipalladium (0), t Bu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.
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