dc.contributor.author |
Brimble, Margaret |
en |
dc.contributor.author |
Rowan, DD |
en |
dc.contributor.author |
Spicer, Julie |
en |
dc.date.accessioned |
2011-09-19T22:56:21Z |
en |
dc.date.issued |
1994 |
en |
dc.identifier.citation |
Australian Journal of Chemistry 47(11): 1979-1988 1994 |
en |
dc.identifier.issn |
0004-9425 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8178 |
en |
dc.description.abstract |
The synthesis of conjugated trienes and related oxidation products of α- farnesene (1), principally from the epoxides of α- farnesene (1), is reported. Base-promoted ring opening of 6,7-epoxide (4) by KOBut/LiNPri2 affords the conjugated triene (2), whilst the 3,4-epoxide (5) affords trienol (7). In contrast, 10,11-epoxide (6) fails to undergo epoxide ring opening; it rearranges to the conjugated triene epoxide (8). Base-promoted ring opening of bisepoxide (9) afforded trienol epoxide (11) at -30°C, whilst cyclization to tetrahydrofurans (10a,b) occurred at room temperature. Photosensitized oxidation of 10,11-epoxide (6) followed by in situ treatment with acid gave the cyclic peroxide (3) and on reduction triol (12). Bisallylic alcohol (13) was prepared by alkylation of 3-methylsulfolene with geranial. Trienes (2) and (3) have been isolated previously as autoxidation products of α- farnesene (1) and are implicated as the causal agents of superficial scald of stored apples. |
en |
dc.language |
EN |
en |
dc.relation.ispartofseries |
Australian Journal of Chemistry |
en |
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0004-9425/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
SUPERFICIAL SCALD |
en |
dc.subject |
APPLES |
en |
dc.title |
Synthesis of Conjugated Trienes and Related Oxidation Products of α-Farnesene |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1071/CH9941979 |
en |
pubs.issue |
11 |
en |
pubs.begin-page |
1979 |
en |
pubs.volume |
47 |
en |
dc.rights.holder |
Copyright: 1994 CSIRO |
en |
pubs.end-page |
1988 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
46137 |
en |
pubs.org-id |
Medical and Health Sciences |
en |
pubs.org-id |
Medical Sciences |
en |
pubs.org-id |
Auckland Cancer Research |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
pubs.record-created-at-source-date |
2010-09-01 |
en |