Abstract
The asymmetric synthesis of cis-7-methoxycalamenene 1 has been accomplished using the intramolecular Buchner reaction of α-diazoketone 7 as the key step in the synthetic route. Upon reduction of the equilibrating azulenone structure 8, the resulting azulenol 9 rearranges to dihydronaphthalene 10 containing the 6,6-membered bicyclic ring system characteristic of 1, by means of an acid-catalyzed aromatization process. Transformation of 10 to 1 is accomplished through a three-step reaction sequence.
| Original language | English |
|---|---|
| Pages (from-to) | 2035-2040 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 77 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 17 Feb 2012 |