Spiroacetal biosynthesis: (+/-)-1,7-dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly).
[reaction: see text] 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.
Schwartz
Brett D
BD
Department of Chemistry, The University of Queensland, Brisbane, Australia 4072, and Institute of Biology, NCSR "D", 15310 Ag. Paraskevi Attikis, Greece.
McErlean
Christopher S P
CS
Fletcher
Mary T
MT
Mazomenos
Basilis E
BE
Konstantopoulou
Maria A
MA
Kitching
William
W
De Voss
James J
JJ
D000818:Animals; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D033621:Tephritidae / Q000378:metabolism*
D013141:Spiro Compounds; C103434:1,7-dioxaspiro(5.5)undecane