IRIS publication 133597374
Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone.
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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 -
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@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} }
Data as stored in IRIS
AUTHORS | McDowell PA, Foley DA, O'Leary P, Ford A, Maguire AR | ||
YEAR | 2012 | ||
MONTH | February | ||
JOURNAL_CODE | The Journal of Organic Chemistry | ||
TITLE | Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone. | ||
STATUS | Published | ||
TIMES_CITED | () | ||
SEARCH_KEYWORD | |||
VOLUME | 77 | ||
ISSUE | 4 | ||
START_PAGE | 2035 | ||
END_PAGE | 2040 | ||
ABSTRACT | 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. | ||
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DOI_LINK | 10.1021/jo202499j | ||
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