Spiroacetal Biosynthesis:  (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera c acuminata and Bactrocera o leae (Olive Fruit Fly)

A biosynthetic scheme rationalizing the formation of (±)-1,7-dioxaspiro[5.5]undecane (5) in the fruit fly species Bactrocera cacuminata and Bactrocera oleae (olive fruit fly) is presented. Incorporation studies with deuterium-labeled keto aldehyde (10), 1,5-nonanediol (11), and 1,5,9-nonanetriol (12...

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Bibliographic Details
Published in:Organic letters 2005-03, Vol.7 (6), p.1173-1176
Main Authors: Schwartz, Brett D, McErlean, Christopher S. P, Fletcher, Mary T, Mazomenos, Basilis E, Konstantopoulou, Maria A, Kitching, William, De Voss, James J
Format: Article
Language:English
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Summary:A biosynthetic scheme rationalizing the formation of (±)-1,7-dioxaspiro[5.5]undecane (5) in the fruit fly species Bactrocera cacuminata and Bactrocera oleae (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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050143w