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Spiroacetal Biosynthesis:  (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly)

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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

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Article Link: https://doi.org/10.1021/ol050143w

Abstract

A 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.

Item Type:Article
Keywords:Lipids, Molecular structure, Organic reactions, Oxidation, Precursors
Subjects:Science > Entomology
Science > Biology > Biochemistry
Live Archive:07 Feb 2024 01:11
Last Modified:07 Feb 2024 01:11

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