Spiroacetal biosynthesis: (±)-1,7-dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (olive fruit fly)

Brett D. Schwartz, Christopher S.P. McErlean, Mary T. Fletcher, Basilis E. Mazomenos, Maria A. Konstantopoulou, William Kitching, James J. De Voss*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1173-1176
Number of pages4
JournalOrganic Letters
Volume7
Issue number6
DOIs
Publication statusPublished - 17 Mar 2005
Externally publishedYes

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