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Total Synthesis of (±)‐Clavilactones A, B, and Proposed D through Iron‐Catalyzed Carbonylation–Peroxidation of Olefin
Author(s) -
Lv Leiyang,
Shen Baojian,
Li Zhiping
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201400326
Subject(s) - carbonylation , olefin fiber , chemistry , diene , catalysis , block (permutation group theory) , organic chemistry , combinatorial chemistry , carbon monoxide , natural rubber , geometry , mathematics
Abstract Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron‐catalyzed carbonylation–peroxidation of a 1,5‐diene. Three steps from aldehydes, alkenes, and tert ‐butylhydroperoxide build up α,β‐epoxy‐γ‐butyrolactone skeleton as a key building block for synthesis of clavilactone family and its derivatives. Based on our results, the structure of the proposed clavilactone D is not correct and requires revision.