Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals

被引：0
|
作者：
Kumar, Rayala Naveen [1 ]
Lee, Seongmin [1 ]
机构：
[1] Univ Texas Austin, Coll Pharm, Div Chem Biol & Med Chem, Austin, TX 78712 USA
来源：
MOLECULES | 2024年 / 29卷 / 23期
基金：
美国国家卫生研究院;
关键词：
hypervalent iodine; spiroiminal; C-H activation; Steroids; C-C; IMMUNOSUPPRESSANT; CYCLOPHILIN; CYCLIZATION; ALKALOIDS; BINDING; ENTRY; SPIROCYCLIZATION; SANGLIFEHRIN; SPIROAMINALS;
D O I：
10.3390/molecules29235812
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)2 and iodine in acetonitrile at 0 degrees C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation.
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页数：11
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