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

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

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 oxidati...

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Veröffentlicht in:Organic letters 2017-01, Vol.19 (2), p.420-423
Hauptverfasser: Iwata, Makoto, Kamijoh, Yuko, Yamamoto, Eri, Yamanaka, Masahiro, Nagasawa, Kazuo
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container_end_page 423
container_issue 2
container_start_page 420
container_title Organic letters
container_volume 19
creator Iwata, Makoto
Kamijoh, Yuko
Yamamoto, Eri
Yamanaka, Masahiro
Nagasawa, Kazuo
description 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.
doi_str_mv 10.1021/acs.orglett.6b03722
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title Total Synthesis of Pyrrole–Imidazole Alkaloid (+)-Cylindradine B
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