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Article: Autoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata

TitleAutoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata
Authors
Issue Date1999
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 1999, v. 55 n. 52, p. 15109-15126 How to Cite?
AbstractPhotooxidation of 4-amorphen-11-ol (1), recently reported as one of the major sesquiterpene natural products from the medicinal plant Fabiana imbricata, results in three allylic hydroperoxides 6, 9 and 10, which are expected from the “ene-type” reaction of molecular oxygen with the tri-substituted double bond in 1. The tertiary allylic hydroperoxide 6 undergoes carbon-carbon bond cleavage and a second autoxidation reaction to yield the more highly oxygenated seco-amorphane 11 under very mild conditions. In acid, this compound may then undergo either a second carbon-carbon bond cleavage reaction to yield nor-sesquiterpenes 2 and 3 (reported as bona fide natural products from F. imbricata, or cyclize to the sesquiterpene peroxofabianane (5), which is a presumed precursor to the natural product fabianane (4). Some mechanistic investigations concerning the two chemical processes: viz:- carbon-carbon bond cleavage and autoxidation which would account for the formation of natural products 2, 3 and 4 from 1 are reported. Tertiary allylic hydroperoxide 32, which lacks the 11-hydroxyl functional group present in 1 undergoes only C-4/C-5 carbon-carbon bond cleavage under more forcing conditions, suggesting a role for this functional group in assisting the autoxidation reactions of 4-amorphen-11-ol.
Persistent Identifierhttp://hdl.handle.net/10722/224559
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991

 

DC FieldValueLanguage
dc.contributor.authorNgo, KS-
dc.contributor.authorBrown, GD-
dc.date.accessioned2016-04-07T07:03:52Z-
dc.date.available2016-04-07T07:03:52Z-
dc.date.issued1999-
dc.identifier.citationTetrahedron, 1999, v. 55 n. 52, p. 15109-15126-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10722/224559-
dc.description.abstractPhotooxidation of 4-amorphen-11-ol (1), recently reported as one of the major sesquiterpene natural products from the medicinal plant Fabiana imbricata, results in three allylic hydroperoxides 6, 9 and 10, which are expected from the “ene-type” reaction of molecular oxygen with the tri-substituted double bond in 1. The tertiary allylic hydroperoxide 6 undergoes carbon-carbon bond cleavage and a second autoxidation reaction to yield the more highly oxygenated seco-amorphane 11 under very mild conditions. In acid, this compound may then undergo either a second carbon-carbon bond cleavage reaction to yield nor-sesquiterpenes 2 and 3 (reported as bona fide natural products from F. imbricata, or cyclize to the sesquiterpene peroxofabianane (5), which is a presumed precursor to the natural product fabianane (4). Some mechanistic investigations concerning the two chemical processes: viz:- carbon-carbon bond cleavage and autoxidation which would account for the formation of natural products 2, 3 and 4 from 1 are reported. Tertiary allylic hydroperoxide 32, which lacks the 11-hydroxyl functional group present in 1 undergoes only C-4/C-5 carbon-carbon bond cleavage under more forcing conditions, suggesting a role for this functional group in assisting the autoxidation reactions of 4-amorphen-11-ol.-
dc.languageeng-
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet-
dc.relation.ispartofTetrahedron-
dc.rightsPosting accepted manuscript (postprint): © <year>. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/-
dc.titleAutoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata-
dc.typeArticle-
dc.identifier.emailBrown, GD: gdbrown@hkucc.hku.hk-
dc.identifier.doi10.1016/S0040-4020(99)00986-2-
dc.identifier.hkuros50055-
dc.identifier.volume55-
dc.identifier.issue52-
dc.identifier.spage15109-
dc.identifier.epage15126-
dc.publisher.placeUnited Kingdom-

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