公开(公告)号：US10081592B2

公开(公告)日：2018-09-25

申请号：US14387028

申请日：2013-03-25

Applicant: THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS ,  Paul J. Hergenrother ,  Robert W. Huigens, III ,  Karen C. Morrison ,  Robert W. Hicklin, II ,  Timothy A. Flood, Jr.

Inventor： Paul J. Hergenrother ,  Robert W. Huigens, III ,  Karen C. Morrison ,  Robert W. Hicklin, II ,  Timothy A. Flood, Jr.

IPC: C07D401/14 ,  C07C69/757 ,  C07D311/94 ,  C07D313/06 ,  C07D223/14 ,  C07D401/04 ,  C07D471/04 ,  C07D471/08 ,  C07D493/08 ,  C07D513/04 ,  C07D519/00 ,  C07D303/10 ,  C07C59/205 ,  C07C62/32 ,  C07C62/38 ,  C07B37/06 ,  C07B37/08 ,  C07D307/93 ,  C07D313/08 ,  C07D405/06 ,  C07D405/12 ,  C07D413/06 ,  C07J21/00 ,  C07J69/00 ,  C07J71/00 ,  C07J73/00 ,  C07J75/00

CPC classification number: C07C69/757 ,  C07B37/06 ,  C07B37/08 ,  C07C59/205 ,  C07C62/32 ,  C07C62/38 ,  C07C2601/16 ,  C07C2602/44 ,  C07C2603/86 ,  C07D223/14 ,  C07D303/10 ,  C07D307/93 ,  C07D311/94 ,  C07D313/06 ,  C07D313/08 ,  C07D401/04 ,  C07D401/14 ,  C07D405/06 ,  C07D405/12 ,  C07D413/06 ,  C07D471/04 ,  C07D471/08 ,  C07D493/08 ,  C07D513/04 ,  C07D519/00 ,  C07J21/008 ,  C07J69/00 ,  C07J71/001 ,  C07J71/0031 ,  C07J73/005 ,  C07J73/008 ,  C07J75/005

Abstract: The invention a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.