Spiroacetals in insects

Francke, W. and Kitching, W. (2001) Spiroacetals in insects. Current Organic Chemistry, 5 2: 233-251. doi:10.2174/1385272013375652

Author Francke, W.
Kitching, W.
Title Spiroacetals in insects
Journal name Current Organic Chemistry   Check publisher's open access policy
ISSN 1385-2728
Publication date 2001
Sub-type Critical review of research, literature review, critical commentary
DOI 10.2174/1385272013375652
Volume 5
Issue 2
Start page 233
End page 251
Total pages 19
Place of publication The Netherlands
Publisher Bentham Science Publishers
Collection year 2001
Language eng
Subject C1
250302 Biological and Medical Chemistry
780103 Chemical sciences
0305 Organic Chemistry
Abstract Spiroacetals, cryptic ketodiols showing a hydroxyl group at both sides of a carbonyl whithin reachable distances are very widespread in nature. A group of 30 different structures, not including stereoisomers, represent volatile, less polar constituents of insect secretions. Five different systems were identified: 1,6-dioxaspirol[4.4]nonanes, 1,6-dioxaspiro[4.5]decanes, 1,6-dioxaspiro[4.6]undecanes, 1,7-dioxaspiro[5.5] undecanes, and 1,7-dioxaspiro[5.6]dodecanes. Some spiroacetals are insect pheromones: (2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane, chalcogran, 1, is a key component of the male produced aggregation pheromone of the spruce bark beetle, Pityogenes cha2cographus. In contrast, (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane, 2, conophthorin, acts as a repellent or spacer in several bark beetles. Racemic 1,7-diosaspiro[5.5]undecane, olean, 5, is the female produced sex pheromone of the olive fly, Bactrocera (Dacus) oleae. The most widespread spiroacetal is 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, 8. Tt often forms a mixture of (E,E)- and (E,Z)-isomers, the (E,E)-isomer showing (2S,6R,8S)-configuration. In the solitary bee, Andrena wilkella, it serves as an aggregation pheromone. Present knowledge on structures and distribution of volatile spiroacetals is comprehensively compiled. Stereochemical aspects and mass spectrometric fragmentation patterns are discussed in detail to facilitate identifications of hitherto unknown compounds. Synthetic approaches to spiroacetals are classified and reviewed. Last but not least, facts and speculations on the biosynthesis of volatile spiroacetals are presented.
Keyword Chemistry, Organic
Olive Fruit-fly
Andrena-haemorrhoa F
Complexation Gas-chromatography
Rectal Gland Secretions
Paravespula-vulgaris L
Principal Aggregation Pheromone
Pityogenes-chalcographus L
Pine-cone Beetle
Q-Index Code C1

Document type: Journal Article
Sub-type: Critical review of research, literature review, critical commentary
Collection: School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 111 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 109 times in Scopus Article | Citations
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Created: Tue, 14 Aug 2007, 15:38:10 EST