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- Publisher Website: 10.1016/S0040-4020(99)00986-2
- Scopus: eid_2-s2.0-0033601448
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Article: Autoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata
Title | Autoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata |
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Authors | |
Issue Date | 1999 |
Publisher | Pergamon. 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? |
Abstract | Photooxidation 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 Identifier | http://hdl.handle.net/10722/224559 |
ISSN | 2023 Impact Factor: 2.1 2023 SCImago Journal Rankings: 0.406 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ngo, KS | - |
dc.contributor.author | Brown, GD | - |
dc.date.accessioned | 2016-04-07T07:03:52Z | - |
dc.date.available | 2016-04-07T07:03:52Z | - |
dc.date.issued | 1999 | - |
dc.identifier.citation | Tetrahedron, 1999, v. 55 n. 52, p. 15109-15126 | - |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.uri | http://hdl.handle.net/10722/224559 | - |
dc.description.abstract | Photooxidation 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.language | eng | - |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet | - |
dc.relation.ispartof | Tetrahedron | - |
dc.rights | Posting 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.title | Autoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata | - |
dc.type | Article | - |
dc.identifier.email | Brown, GD: gdbrown@hkucc.hku.hk | - |
dc.identifier.doi | 10.1016/S0040-4020(99)00986-2 | - |
dc.identifier.scopus | eid_2-s2.0-0033601448 | - |
dc.identifier.hkuros | 50055 | - |
dc.identifier.volume | 55 | - |
dc.identifier.issue | 52 | - |
dc.identifier.spage | 15109 | - |
dc.identifier.epage | 15126 | - |
dc.identifier.isi | WOS:000084108200027 | - |
dc.publisher.place | United Kingdom | - |
dc.identifier.issnl | 0040-4020 | - |