
%0 Journal Article
%A Brimble, MA 
%A Rowan, DD 
%A Spicer, JA 
%T Synthesis of Conjugated Trienes and Related Oxidation Products of &#945;-Farnesene
%J Australian Journal of Chemistry
%D 1994/11/01
%V 47
%N 11
%P 1979-1988
%K 
%R https://doi.org/10.1071/CH9941979
%U https://www.publish.csiro.au/paper/CH9941979 
%X The synthesis of conjugated trienes and related oxidation products of &#945;- farnesene (1), principally from the epoxides of &#945;- 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&#176;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 &#945;- farnesene (1) and are implicated as the causal agents of superficial scald of stored apples. 
