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. 2009 Mar 19;11(6):1297-300.
doi: 10.1021/ol900071c.

Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp

Sachiko Tsukamoto  1 , Tetsuro Kawabata, Hikaru Kato, Thomas J Greshock, Hiroshi Hirota, Tomihisa Ohta, Robert M Williams
Affiliations

Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp

Sachiko Tsukamoto et al. Org Lett. .

Abstract

Antipodal (-)-versicolamide B and notoamides L-N were isolated from a marine-derived Aspergillus sp. The possible biosynthetic pathway of enantiomeric pairs of notoamide B and versicolamide B are proposed. Notoamide L is the first metabolite containing 25 carbons in the related prenylated indole alkaloids. Notoamide M is potentially a precursor to the proposed azadiene species involved in the putative intramolecular Diels-Alder reaction in the biogenesis of the bicyclo[2.2.2]diazaoctane ring system.

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Figures

Figure 1
Figure 1
Structures of compounds from the marine-derived Aspergillus sp.
Figure 2
Figure 2
Structures of three pairs of enantiomeric alkaloids isolated from the marine-derived Aspergillus sp. and the terrestrial Aspergillus versicolor.
Scheme 1
Scheme 1
Possible biogenesis of the enantiomeric pairs of notoamide B (2, 7) and versicolamide B (9, 10).
Scheme 2
Scheme 2
Possible formation of the bicyclo[2.2.2]diazaoctane ring system.
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References

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    1. Tsukamoto S, Kato H, Greshock TJ, Hirota H, Ohta T, Williams RM. submitted.
    1. Tsukamoto S, Kato H, Samizo M, Nojiri Y, Onuki H, Hirota H, Ohta T. J Nat Prod. 2008;71:2064–2067. - PubMed

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