Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone.

Typeset version

 

TY  - JOUR
  - McDowell PA, Foley DA, O'Leary P, Ford A, Maguire AR
  - 2012
  - February
  - The Journal of Organic Chemistry
  - Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone.
  - Published
  - ()
  - 77
  - 4
  - 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.
  - 10.1021/jo202499j
DA  - 2012/02
ER  - 
@article{V133597374,
   = {McDowell PA,  Foley DA and  O'Leary P,  Ford A and  Maguire AR },
   = {2012},
   = {February},
   = {The Journal of Organic Chemistry},
   = {Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone.},
   = {Published},
   = {()},
   = {77},
   = {4},
  pages = {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.}},
   = {10.1021/jo202499j},
  source = {IRIS}
}
AUTHORSMcDowell PA, Foley DA, O'Leary P, Ford A, Maguire AR
YEAR2012
MONTHFebruary
JOURNAL_CODEThe Journal of Organic Chemistry
TITLEAsymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone.
STATUSPublished
TIMES_CITED()
SEARCH_KEYWORD
VOLUME77
ISSUE4
START_PAGE2035
END_PAGE2040
ABSTRACTThe 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.
PUBLISHER_LOCATION
ISBN_ISSN
EDITION
URL
DOI_LINK10.1021/jo202499j
FUNDING_BODY
GRANT_DETAILS