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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).