Asymmetric Synthesis of (-)-Aurantioclavine via Palladium-Catalyzed Intramolecular Allylic Amination

作者：Suetsugu Satoshi; Nishiguchi Hiromi; Tsukano Chihiro; Takemoto Yoshiji^*

来源：Organic Letters, 2014, 16(3): 996-999.

DOI：10.1021/ol4037314

The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 9596 enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.

• 出版日期2014-2-7