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Regioselective Oxidative Ring Cleavage of a Phlorin Analogue: An Approach for Synthesizing Linear Tetrapyrroles

Author:
Shao, Jiewei, Li, Chengjie, Kong, Jiahui, Jiang, Haoran, Zhao, Shuangliang, Li, Minzhi, Liang, Xu, Zhu, Weihua, Xie, Yongshu
Source:
Organic letters 2018 v.20 no.7 pp. 1941-1944
ISSN:
1523-7052
Subject:
crystal structure, ferric chloride, moieties, organic compounds, oxidation, regioselectivity, zinc
Abstract:
Oxidation of neo-N-confused phlorin 1 with excessive FeCl₃ leads to regioselective ring opening, generating three linear tetrapyrroles, i.e., (10Z,15Z)-biladienone 2, (10Z,15E)-biladienone 3, and 19-methoxy (10Z,15E)-biladiene 4 with an overall yield of 88%. The coordination of these compounds with Zn(II) is affected by the inverted terminal pyrrolic unit, and the presence of the electron-withdrawing keto moiety. The structural identities were also clearly elucidated by the crystal structures of 3 and 4-Zn and were rationalized by DFT calculations.
Agid:
6083717