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Isolation of Antipodal (-)-versicolamide B and Notoamides L-N from a Marine-derived Aspergillus Sp

Overview
Journal Org Lett
Publisher American Chemical Society
Specialties Biochemistry
Chemistry
Date 2009 Mar 14
PMID 19281134
Citations 33
Authors
Sachiko Tsukamoto
Tetsuro Kawabata
Hikaru Kato
Thomas J Greshock
Hiroshi Hirota
Tomihisa Ohta
Robert M Williams
Affiliations
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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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References
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Greshock T, Grubbs A, Tsukamoto S, Williams R . A concise, biomimetic total synthesis of stephacidin A and notoamide B. Angew Chem Int Ed Engl. 2007; 46(13):2262-5. DOI: 10.1002/anie.200604378. View
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Tsukamoto S, Kato H, Samizo M, Nojiri Y, Onuki H, Hirota H . Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp. J Nat Prod. 2008; 71(12):2064-7. DOI: 10.1021/np800471y. View
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Grubbs A, Artman 3rd G, Tsukamoto S, Williams R . A concise total synthesis of the notoamides C and D. Angew Chem Int Ed Engl. 2007; 46(13):2257-61. DOI: 10.1002/anie.200604377. View
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Kato H, Yoshida T, Tokue T, Nojiri Y, Hirota H, Ohta T . Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. Angew Chem Int Ed Engl. 2007; 46(13):2254-6. DOI: 10.1002/anie.200604381. View
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Greshock T, Grubbs A, Jiao P, Wicklow D, Gloer J, Williams R . Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600. Angew Chem Int Ed Engl. 2008; 47(19):3573-7. PMC: 2829633. DOI: 10.1002/anie.200800106. View