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Efficient construction of the oxatricyclo[6.3.1.0(0,0)]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate.
Org Lett. 2005 Aug 18; 7(17):3725-7.OL

Abstract

The rhodium(II)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures. [reaction: see text]

Authors+Show Affiliations

Padwa A
Department of Chemistry, Emory University, Atlanta, GA 30322, USA. chemap@emory.edu
Boonsombat J
No affiliation info available
Rashatasakhon P
No affiliation info available
Willis J
No affiliation info available

MeSH

AlkanesCatalysisCyclizationDiterpenesMolecular StructureQuinonesRhodiumTemperature

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

16092860

Citation

Padwa, Albert, et al. "Efficient Construction of the Oxatricyclo[6.3.1.0(0,0)]dodecane Core of Komaroviquinone Using a Cyclization/cycloaddition Cascade of a Rhodium Carbenoid Intermediate." Organic Letters, vol. 7, no. 17, 2005, pp. 3725-7.
Padwa A, Boonsombat J, Rashatasakhon P, et al. Efficient construction of the oxatricyclo[6.3.1.0(0,0)]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate. Org Lett. 2005;7(17):3725-7.
Padwa, A., Boonsombat, J., Rashatasakhon, P., & Willis, J. (2005). Efficient construction of the oxatricyclo[6.3.1.0(0,0)]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate. Organic Letters, 7(17), 3725-7.
Padwa A, et al. Efficient Construction of the Oxatricyclo[6.3.1.0(0,0)]dodecane Core of Komaroviquinone Using a Cyclization/cycloaddition Cascade of a Rhodium Carbenoid Intermediate. Org Lett. 2005 Aug 18;7(17):3725-7. PubMed PMID: 16092860.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient construction of the oxatricyclo[6.3.1.0(0,0)]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate. AU - Padwa,Albert, AU - Boonsombat,Jutatip, AU - Rashatasakhon,Paitoon, AU - Willis,Jerremey, PY - 2005/8/12/pubmed PY - 2006/7/4/medline PY - 2005/8/12/entrez SP - 3725 EP - 7 JF - Organic letters JO - Org Lett VL - 7 IS - 17 N2 - The rhodium(II)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16092860/Efficient_construction_of_the_oxatricyclo[6_3_1_0_00_]dodecane_core_of_komaroviquinone_using_a_cyclization/cycloaddition_cascade_of_a_rhodium_carbenoid_intermediate_ DB - PRIME DP - Unbound Medicine ER -