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词条 Versicolamide B
释义

  1. References

(-)-Versicolamide B and (+)-Versicolamide B are spiroindole alkaloids isolated from the fungus Aspergillus that belong to a class of naturally occurring 2,5-diketopiperazines.[1] The versicolamides are structurally complex spiro-cyclized versions of prenylated cyclo(L-Trp-L-Pro) derivatives which possess a unique spiro-fusion to a pyrrolidine at the 3-position of the oxindole core together with the bicyclo[2.2.2]diazaoctane ring system. While (-)-versicolamide B was isolated from the marine fungus Aspergillus sp. [2] the enantiomer (+)-versicolamide B was isolated from the terrestrial fungi Aspergillus versicolor NRRL.[3]

The total asymmetric syntheses of both enantiomers have been achieved and the implications of their biosynthesis have been investigated.[4]

References

1. ^{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = May 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}}
2. ^{{cite journal |vauthors=Tsukamoto S, Kawabata T, Kato H, Greshock TJ, Hirota H, Ohta T, Williams RM | title = Isolation of Antipodal (−)-Versicolamide B and Notoamides L− N from a Marine-Derived Aspergillus sp | journal = Organic Letters | volume = 11 | issue = 6 | pages = 1297–1300 | date= February 2009 | pmid = 19281134| doi = 10.1021/ol900071c | url = | pmc=2829632}}
3. ^{{cite journal |vauthors=Greshock TJ, Grubbs AW, Jiao P, Wicklow DT, Gloer JB, Williams RM | title = 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 | journal = Angewandte Chemie International Edition | volume = 47 | issue = 19 | pages = 3573–3577 | date= April 2008 | pmid = 18389509 | doi = 10.1002/anie.200800106 | url = | pmc=2829633}}
4. ^{{cite journal |vauthors=Miller KA, Tsukamoto S, Williams RM | title = Asymmetric total syntheses of (+)-and (−)-versicolamide B and biosynthetic implications | journal = Nature Chemistry | volume = 1 | issue = 1 | pages = 63–68 | date= April 2009 | pmid = 20300443 | doi = 10.1038/nchem.110 | url = | pmc=2840645}}

2 : Alkaloids|Diketopiperazines

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