Studies towards the synthesis of Aspergillitine, a unique tricyclic angular chromone from Aspergillus versicolor

Studies towards the synthesis of Aspergillitine, a unique tricyclic angular chromone from Aspergillus versicolor

Simonetti, Sebastian O.; Larghi, Enrique L.; Kaufman, Teodoro S.

Abstract:

Aspergillus versicolor is a ubiquitous fungus. Recently, the group of Proksch studied a strain of A. versicolor from the marine sponge Xestospongia exigua, isolating aspergillitine (1) and the aspergiones A-F (2a-f) as novel tricyclic angular chromones (Fig 1). Aspergillitine is unique because incorporation of a nitrogen atom in polyketides is rare, being known only few cases, such as bostricoydine (3). On the other side, it was demonstrated that the structures originally assigned to 2a and 2b correspond to 4a and 4b. There is a distinct possibility that the structure of aspergillitine should be corrected and assigned to 5. An unambiguous synthesis of 1 is thus required.

Aspergillus versicolor is a ubiquitous fungus. Recently, the group of Proksch studied a strain of A. versicolor from the marine sponge Xestospongia exigua, isolating aspergillitine (1) and the aspergiones A-F (2a-f) as novel tricyclic angular chromones (Fig 1). Aspergillitine is unique because incorporation of a nitrogen atom in polyketides is rare, being known only few cases, such as bostricoydine (3). On the other side, it was demonstrated that the structures originally assigned to 2a and 2b correspond to 4a and 4b. There is a distinct possibility that the structure of aspergillitine should be corrected and assigned to 5. An unambiguous synthesis of 1 is thus required.

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DOI: 10.5151/chempro-14bmos-R0386-1

Referências bibliográficas

• [1] 1 Lin, W. H.; Brauers, G.; Ebel, R.; Wray, V.; Berg, A.; Proksch, P. J. Nat. Prod. 2003, 66, 57.
• [2] 2 a) Saito, F.; Kuramochi, K.; Nakazaki, A.; Mizushina, Y.; Sugawara, F.; Kobayashi, S. Eur. J. Org. Chem. 2006, 4796; b) Kuramochi, K.; Saito, F.; Nakazaki, T.; Takeuchi, T.; Tsubaki, K.; Sugawara, F.; Kobayashi, S. Biosci. Biotechnol. Biochem. 2010, 74, 1635.

Como citar:

Simonetti, Sebastian O.; Larghi, Enrique L.; Kaufman, Teodoro S.; "Studies towards the synthesis of Aspergillitine, a unique tricyclic angular chromone from Aspergillus versicolor", p-386-386. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0386-1