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Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction
Author(s) -
Alonso Pedro,
Pardo Pilar,
Fontaneda Raquel,
Fañanás Francisco J.,
Rodríguez Félix
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702490
Subject(s) - cationic polymerization , halogen , chemistry , halide , enyne , organic chemistry , combinatorial chemistry , natural product , reaction conditions , catalysis , alkyl
The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid‐mediated cationic cyclisation reaction is disclosed. This high‐yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen‐containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9‐ epi ‐Ambrox demonstrates the potential of the reaction for natural product synthesis.