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DOI: 10.1055/s-0041-1738197
Total Synthesis of (±)-Ishwarane
Carbon Atom Insertion: An Efficient Synthesis of Ishwarane.
J. Chem. Soc., Chem. Comm. 1977; 587-588
DOI: 10.1039/C39770000587.
Key words
(±)-ishwarane - Robinson annulation - conjugate addition - Grignard addition - cyclopropanation - carbene C–H insertion
Significance
Ishwarane is a sesquiterpene featuring a carbon skeleton with an intriguing tricyclo[3.2.1.02,7]octane core. After the first total synthesis of ishwarane reported by Kelly and co-workers in 1970/1971 (J. Chem. Soc. D 1970, 1102; J. Chem. Soc. D 1971, 479), Cory and co-workers present a highly efficient six-step sequence to the natural product exploiting carbon atom insertion.
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Comment
Previously reported octalone D is rapidly elaborated into cis-decaline F through conjugate addition, Grignard addition, and dehydration. A cyclopropanation and C–H insertion cascade via putative carbene intermediate G yields (±)-ishwarane.
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Publication History
Article published online:
17 May 2022
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