Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media
Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (−)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here,...
Saved in:
Published in | Journal of organic chemistry Vol. 83; no. 23; pp. 14457 - 14464 |
---|---|
Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
07.12.2018
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (−)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (−)-azaspirene skeleton easily racemizes in neutral aqueous media. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b02223 |