Spiroacetal Biosynthesis: (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly)View Altmetrics View AltmetricsTools Schwartz, B. D., McErlean, C. S.P., Fletcher, M. T., Mazomenos, B. E., Konstantopoulou, M. A., Kitching, W. and De Voss, J. J. (2005) Spiroacetal Biosynthesis: (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly). Organic Letters, 7 (6). pp. 1173-1176. ISSN 1523-7060 Full text not currently attached. Access may be available via the Publisher's website or OpenAccess link. Article Link: https://doi.org/10.1021/ol050143w AbstractA biosynthetic scheme rationalizing the formation of (±)-1,7-dioxaspiro[5.5]undecane (5) in the fruit fly species Bactrocera cacuminata and Bactroceraoleae (olive fruit fly) is presented. Incorporation studies with deuterium-labeled keto aldehyde (10), 1,5-nonanediol (11), and 1,5,9-nonanetriol (12), and our previous finding that both oxygen atoms of 5 originate from dioxygen, are strongly evidentiary. The racemic condition of the natural spiroacetal 5 is accounted for, and inter alia, it is demonstrated that dihydropyran (18) is not an important intermediate en route to 5.
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