TY - JOUR
T1 - Spiroacetal biosynthesis
T2 - (±)-1,7-dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (olive fruit fly)
AU - Schwartz, Brett D.
AU - McErlean, Christopher S.P.
AU - Fletcher, Mary T.
AU - Mazomenos, Basilis E.
AU - Konstantopoulou, Maria A.
AU - Kitching, William
AU - De Voss, James J.
PY - 2005/3/17
Y1 - 2005/3/17
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=18244385975&partnerID=8YFLogxK
U2 - 10.1021/ol050143w
DO - 10.1021/ol050143w
M3 - Article
SN - 1523-7060
VL - 7
SP - 1173
EP - 1176
JO - Organic Letters
JF - Organic Letters
IS - 6
ER -