Peer-Reviewed Journal Details
Mandatory Fields
McDowell, PA,Foley, DA,O'Leary, P,Ford, A,Maguire, AR
2012
February
Journal Of Organic Chemistry
Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone
Published
()
Optional Fields
AMINO-ACIDS SESQUITERPENES STEREOCONTROL
77
2035
2040
The asymmetric synthesis of cis-7-methoxycalamenene 1 has been accomplished using the intramolecular Buchner reaction of a-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.
DOI 10.1021/jo202499j
Grant Details
Publication Themes