67601-05-2Relevant articles and documents
Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants
Partridge, Suzanne J.,Withall, David M.,Caulfield, John C.,Pickett, John A.,Stockman, Robert A.,Oldham, Neil J.,Birkett, Michael A.
supporting information, p. 7231 - 7234 (2021/04/21)
Biosynthesis of (1R,4aS,7S,7aR)-nepetalactol (1) and (4aS,7S,7aR)-nepetalactone (2) in plants involves iridoid synthase (ISY), an atypical reductive cyclase that catalyses the reduction of 8-oxogeranial into the reactive enol of (S)-8-oxocitronellal, and cyclization of this enol intermediate, either non-enzymatically or by a nepetalactol-related short chain dehydrogenase enzyme (NEPS) that yields the nepetalactols. In this study, we investigated the biosynthesis in vivo of 1 and 2 in the pea aphid, Acyrthosiphon pisum, using a library of isotopically-labelled monoterpenoids as molecular probes. Topical application of deuterium-labelled probes synthesized from geraniol and nerol resulted in production of 2H4?lactol 1 and 2H4?lactone 2. However, deuterium incorporation was not evident using labelled probes synthesized from (S)-citronellol. These results suggest that iridoid biosynthesis in animals, specifically aphids, may follow a broadly similar route to that characterised for plants.
Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 6,14-dimethyl-2-octadecanone, and 14-methyl-2-octadecanone, the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma
Mori, Kenji
scheme or table, p. 2798 - 2805 (2009/08/15)
All of the stereoisomers of the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma, were synthesized. They are (R)- and (S)-6-methyl-2-octadecanone, (6R,14R)-, (6R,14S)-, (6S,14R)-, and (6S,14S)-6,14-dimethyl-2-octadecanone, and (R)- and (S)-14-methyl-2-octadecanone. Enantiomers of citronellal and methyl (S)-3-hydroxy-2-methylpropanoate were the starting materials, and olefin cross metathesis was employed as the key reaction.
Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: Application to enantiomeric syntheses of tribolure and a marine fatty acid
Sankaranarayanan,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1373 - 1378 (2007/10/03)
A convenient synthesis of the title chiron antipodes has been developed starting from (±)-citronellol via a sequential acetylation protocol using two lipases. The different stereoisomers of the chiron were then functionalized by simple routes to (4R,8R)-dimethyldecanal, an insect pheromone and (5R,9R)-5,9,13-trimethyltetradecanoic acid, a marine phospholipid fatty acid.
