Total synthesis of (+)-Sch 725680: inhibitor of mammalian A-, B-, and Y-family DNA polymerases

Toshifumi Takeuchi; Yoshiyuki Mizushina; Satoshi Takaichi; Natsuki Inoue; Kouji Kuramochi; Satomi Shimura; Yusuke Myobatake; Yuri Katayama; Kenji Takemoto; Shogo Endo; Shinji Kamisuki; Fumio Sugawara

doi:10.1021/ol301865u

Total synthesis of (+)-Sch 725680: inhibitor of mammalian A-, B-, and Y-family DNA polymerases

Org Lett. 2012 Sep 7;14(17):4303-5. doi: 10.1021/ol301865u. Epub 2012 Aug 28.

Authors

Toshifumi Takeuchi¹, Yoshiyuki Mizushina, Satoshi Takaichi, Natsuki Inoue, Kouji Kuramochi, Satomi Shimura, Yusuke Myobatake, Yuri Katayama, Kenji Takemoto, Shogo Endo, Shinji Kamisuki, Fumio Sugawara

Affiliation

¹ Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda-shi, Chiba 278-8510, Japan.

PMID: 22928597
DOI: 10.1021/ol301865u

Abstract

The total synthesis of (+)-Sch 725680, a member of the hydrogenated azaphilone family, has been accomplished. The synthesis confirmed the absolute configuration and biological activities of the natural product. A key reaction to construct a hydrogenated azaphilone core skeleton is a Ti-mediated aldol reaction.

MeSH terms

Aspergillus / chemistry
Benzopyrans / chemical synthesis*
Benzopyrans / chemistry
Benzopyrans / pharmacology*
Molecular Structure
Nucleic Acid Synthesis Inhibitors*
Stereoisomerism

Substances

Benzopyrans
Nucleic Acid Synthesis Inhibitors
Sch 725680