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. 2008;47(19):3573-7.
doi: 10.1002/anie.200800106.

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

Thomas J Greshock  1 , Alan W Grubbs, Ping Jiao, Donald T Wicklow, James B Gloer, Robert M Williams
Affiliations

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

Thomas J Greshock et al. Angew Chem Int Ed Engl. 2008.
No abstract available

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Figures

Scheme 1
Scheme 1
Structures of several members of the paraherquamide/stephacidin/brevianamide family of prenylated indole alkaloids.
Scheme 2
Scheme 2
Syn- and anti-relative configurations at C-19 of the bicyclo[2.2.2]diazaoctane ring system (sclerotiamide numbering).
Scheme 3
Scheme 3
CD spectra of Aspergillus versicolor NRRL 35600 metabolites: (a) ent-(−)-stephacidin A; (b) ent-(+)-notoamide B; (c) versicolamide B. All CD spectra were recorded in 1:1 CH2Cl2:MeOH.
Scheme 4
Scheme 4
Synthesis of d,l-6 and d,l-8. Structures are depicted with the correct relative and absolute configuration for the natural materials isolated from Aspergillus versicolor NRRL 35600; all substances after 11 were produced in racemic form.
Scheme 5
Scheme 5
Some possible biosynthetic relationships.
See this image and copyright information in PMC

References

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