Coibacins A and B: Total Synthesis, Stereochemical Revision and Structural Elucidation

Coibacins A and B: Total Synthesis, Stereochemical Revision and Structural Elucidation

Avila, Carolina M.; Carneiro, Vânia M. T.; Balunas, Marcy J.; Gerwick, William H.; Pilli, Ronaldo A.

Abstract:

Coibacins A (1) and B (2) are polyketides isolated from a Panamanian marine cyanobacterium Oscillatoria sp. that display antileishmanial activity. The absolute configuration of the dihydropyran-2- one moiety (C-5) was assigned to be S, based on circular dichroism (CD), while only the trans relative stereochemistry of the cyclopropyl ring was determined by NMR. We embarked on the total synthesis of stereoisomers of coibacin A (1) aiming to establish its absolute configuration. Additionally, we have synthesized the natural isomer of coibacin B (2).

Coibacins A (1) and B (2) are polyketides isolated from a Panamanian marine cyanobacterium Oscillatoria sp. that display antileishmanial activity. The absolute configuration of the dihydropyran-2- one moiety (C-5) was assigned to be S, based on circular dichroism (CD), while only the trans relative stereochemistry of the cyclopropyl ring was determined by NMR. We embarked on the total synthesis of stereoisomers of coibacin A (1) aiming to establish its absolute configuration. Additionally, we have synthesized the natural isomer of coibacin B (2).

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013827203418

Referências bibliográficas

• [1] 1Balunas, M. J.; et al. Org. Lett. 2012, 14, 3878.
• [2] 2Crimmins, M. T.; King, B. W. J. Am. Chem. Soc. 1998, 120, 9084.
• [3] 3 Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1994, 116, 2651.

Como citar:

Avila, Carolina M.; Carneiro, Vânia M. T.; Balunas, Marcy J.; Gerwick, William H.; Pilli, Ronaldo A.; "Coibacins A and B: Total Synthesis, Stereochemical Revision and Structural Elucidation", p-203-203. 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_2013827203418