Synthesis of all possible stereoisomers of 6,10,13- trimethyltetradecan-2-one, male-produced sex pheromone of Pallantia macunaima

Synthesis of all possible stereoisomers of 6,10,13- trimethyltetradecan-2-one, male-produced sex pheromone of Pallantia macunaima

Soldi, Rafael A.; Zarbin, Paulo H.G.

Abstract:

Pallantia macunaima (Heteroptera, Pentatomidae) is one important heteropteran pest found in southern Bazil. Previously, we reported the structural elucidation, synthesis and absolute configuration of sex pheromone for this species. The male-specific compound was identified as (6R,10S)-6,10-13-trimethyltetradecan-2-one ((6R,10S)-1), the first ketone pheromone described in stink bugs. Here in, we wish to describe an alternative methodology to prepare all isomers of 6,10,13-trimethyltetradecan-2-one.

Pallantia macunaima (Heteroptera, Pentatomidae) is one important heteropteran pest found in southern Bazil. Previously, we reported the structural elucidation, synthesis and absolute configuration of sex pheromone for this species. The male-specific compound was identified as (6R,10S)-6,10-13-trimethyltetradecan-2-one ((6R,10S)-1), the first ketone pheromone described in stink bugs. Here in, we wish to describe an alternative methodology to prepare all isomers of 6,10,13-trimethyltetradecan-2-one.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391512371

Referências bibliográficas

• [1] 1Favaro, C.F.; Soldi, R.A.; Ando, T.; Zarbin, P.H.G.Org. Lett. 2013, 15,1822
• [2] 2Santagelo, E.M.; Zarbin, P.H.G.; Cass, Q.B.; Corrêa, A.G. Synth Commum. 2001, 31, 3685
• [3] 3Nakamura, Y.; Mori, K. Eur. Jour. Org. Chem. 2000, 15, 2745
• [4] 4Taguri, T.; Yamakawa, R.; Ando, T.Tetrahedron Asymm 2012, 23, 852.

Como citar:

Soldi, Rafael A.; Zarbin, Paulo H.G.; "Synthesis of all possible stereoisomers of 6,10,13- trimethyltetradecan-2-one, male-produced sex pheromone of Pallantia macunaima", p-86-86. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391512371