A Chemoenzymatic Approach to C1-C6 Fragment of (−)-Putaminoxin

A Chemoenzymatic Approach to C1-C6 Fragment of (−)-Putaminoxin

Vassiliades, Sandra V.; Bianco, Graziela G.; Jr., Luiz S. Longo

Abstract:

(−)-Putaminoxin (1) is a decalactone isolated from the culture filtrates of the fungus Phoma putaminum, a leaf necrosis agent of the weed Erigeron annuus. These and other structure related compounds showed significant phytotoxic activity against several plants. Herein we describe our efforts to the synthesis of the C1-C6 fragment of the title compound [(S)-5-hydroxyhept-6-enoic acid (2)], using a kinetic enzymatic resolution approach as key step.

(−)-Putaminoxin (1) is a decalactone isolated from the culture filtrates of the fungus Phoma putaminum, a leaf necrosis agent of the weed Erigeron annuus. These and other structure related compounds showed significant phytotoxic activity against several plants. Herein we describe our efforts to the synthesis of the C1-C6 fragment of the title compound [(S)-5-hydroxyhept-6-enoic acid (2)], using a kinetic enzymatic resolution approach as key step.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0210-1

Referências bibliográficas

• [1] 1 Evidente, A.; Lanzetta, R.; Capasso, R.; Andolfi, A.; Bottalico, A.; Vurro, M.; Zonno, M. C. Phytochemistry 1995, 40, 1637.
• [2] 2 For the first total synthesis of (-)-1 see: Sabitha, G.; Swapna, K. Y. R.; Yadav, S. J. Tetrahedron Lett. 2009, 50, 5417.
• [3] 3 Vurro, M.; Ellis, B. E. Plant Sci. 1997, 126, 29.
• [4] 4 Vilalba, B. T.; Bianco, G.G.; Longo, Jr. L. S. In: 34ª RASBQ; Águas de Lindóia, SP, Brazil. 28-30 May, 2010.

Como citar:

Vassiliades, Sandra V.; Bianco, Graziela G.; Jr., Luiz S. Longo; "A Chemoenzymatic Approach to C1-C6 Fragment of (−)-Putaminoxin", p-210-210. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0210-1