Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

Paul A. McDowell; David A. Foley; Patrick O'Leary; Alan Ford; Anita R. Maguire

doi:10.1021/jo202499j

Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

Paul A. McDowell, David A. Foley, Patrick O'Leary, Alan Ford, Anita R. Maguire

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

24 Citations (Scopus)

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	https://doi.org/10.1021/jo202499j
Publication status	Published - 17 Feb 2012
Externally published	Yes

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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.",

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AU - McDowell, Paul A.

AU - Foley, David A.

AU - O'Leary, Patrick

AU - Ford, Alan

AU - Maguire, Anita R.

PY - 2012/2/17

Y1 - 2012/2/17

N2 - 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.

AB - 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.

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JO - Journal of Organic Chemistry

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IS - 4

ER -

Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

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