Total Synthesis of (±)‐Alopecuridine and Its Biomimetic Transformation into (±)‐Sieboldine A | Zendy

Zhang XiaoMing | Zendy; Tu YongQiang | Zendy; Zhang FuMin | Zendy; Shao Hui | Zendy; Meng Xing | Zendy

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Total Synthesis of (±)‐Alopecuridine and Its Biomimetic Transformation into (±)‐Sieboldine A

Author(s) -

Zhang XiaoMing,

Tu YongQiang,

Zhang FuMin,

Shao Hui,

Meng Xing

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201008147

Subject(s) - total synthesis , intramolecular force , pinacol , ring (chemistry) , sequence (biology) , transformation (genetics) , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , gene

The features you need : The first total synthesis of lycopodium alkaloid alopecuridine has been achieved in 13 steps in the longest linear sequence, and its biomimetic conversion into sieboldine A has been validated through a two‐step oxidation. The synthesis features a semipinacol rearrangement of a functionalized medium‐sized ring and an intramolecular pinacol coupling mediated by SmI 2 (see scheme; Boc= tert ‐butoxycarbonyl).

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