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Total Synthesis of (+)‐Myomontanone and (+)‐10,11‐Didehydromyomontanone
Author(s) -
Roussis Vassilios,
Hubert Terrance D.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920193
Subject(s) - chemistry
The sesquiterpenoid (+)‐myomontanone ( 2 ), a toxic component of the Australian plant Myoporum montanum , has been synthesized through a short efficient sequence. An electrochemical oxyselenation‐deselenation sequence allows oxidation of an intermediate olefin, in the presence of the furan ring, ultimatively providing the requisite enone of the natural product. This approach also allowed synthesis of (+)‐10,11‐didehydromyomontanone ( 13 ) and several other natural products of this family of furanosesquiterpenoids.