Synthesis of (R/S)-2-hydroxy-5-methyl-hexan-3-one, sinomone issued by Araceae species: P. acutatum and T. ulei

Synthesis of (R/S)-2-hydroxy-5-methyl-hexan-3-one, sinomone issued by Araceae species: P. acutatum and T. ulei

Filho, Everaldo F. Santos; Maia, Artur C. D.; Navarro, Daniela M. A. F.; Princival, Jefferson L.

Abstract:

In the northeast of Brazil, the strongly fragrant Araceae species: Taccarum ulei and Philodendron acutatum emit a floral scent called (S)-2-hydroxy-5- methyl-hexan-3-one ((S)-1). This compound (S)-1 is highly attractive to night active pollinators scarab beetles of the tribe Cyclocephalini (Figure 1). Herein, we describe the synthesis of the racemic acyloin (R/S)-1 from the aminoacid L-leucine as starting material.

In the northeast of Brazil, the strongly fragrant Araceae species: Taccarum ulei and Philodendron acutatum emit a floral scent called (S)-2-hydroxy-5- methyl-hexan-3-one ((S)-1). This compound (S)-1 is highly attractive to night active pollinators scarab beetles of the tribe Cyclocephalini (Figure 1). Herein, we describe the synthesis of the racemic acyloin (R/S)-1 from the aminoacid L-leucine as starting material.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013915194734

Referências bibliográficas

• [1] 1(a) Maia, A. C. D.; Gibernau, M.; Carvalho, A. T.; Gonçalves, E. G.; Schlindwein,
• [2] C. Biol. J. Linnean Soc., 2013, 108, 22; (b) Maia, A. C. D; Gibernau, M; Dotterl,
• [3] S.; Navarro, D. M. A. F.; Seifert, K.; Muller, T.; Schlindwein, C. Phytochem.
• [4] 2013, 93, 71.
• [5] 2 Houston, T. A; Wilkinson, B. L Blanchfield, J. T. Org. Lett. 2004, 6, 679

Como citar:

Filho, Everaldo F. Santos; Maia, Artur C. D.; Navarro, Daniela M. A. F.; Princival, Jefferson L.; "Synthesis of (R/S)-2-hydroxy-5-methyl-hexan-3-one, sinomone issued by Araceae species: P. acutatum and T. ulei", p-267-267. 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_2013915194734