Total Synthesis of Pyrrole-Imidazole Alkaloid (+)-Cylindradine B

Makoto Iwata; Yuko Kamijoh; Eri Yamamoto; Masahiro Yamanaka; Kazuo Nagasawa

doi:10.1021/acs.orglett.6b03722

Total Synthesis of Pyrrole-Imidazole Alkaloid (+)-Cylindradine B

Org Lett. 2017 Jan 20;19(2):420-423. doi: 10.1021/acs.orglett.6b03722. Epub 2017 Jan 5.

Authors

Makoto Iwata¹, Yuko Kamijoh¹, Eri Yamamoto², Masahiro Yamanaka², Kazuo Nagasawa¹

Affiliations

¹ Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei City, Tokyo 184-8588, Japan.
² Department of Chemistry, Faculty of Science, Rikkyo University , 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.

PMID: 28054786
DOI: 10.1021/acs.orglett.6b03722

Abstract

Cylindradines A and B are members of the oroidin-derived pyrrole-imidazole alkaloid (PIA) family. They possess a characteristic pyrrole-3-carbamoyl moiety, which is unusual among PIAs. We achieved a total synthesis of (+)-cylindradine B by applying a Pictet-Spengler-type reaction followed by oxidative cyclization in the presence of hypervalent iodine to construct the pyrrole-3-carbamoyl and cyclic guanidine with N,N'-aminal moieties at C6 and C10.

Publication types

Research Support, Non-U.S. Gov't