4.7 Article

Xestoproxamines A-C from Neopetrosia proxima. Assignment of Absolute Stereostructure of Bis-piperidine Alkaloids by Integrated Degradation-CD Analysis

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 74, Issue 3, Pages 430-440

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/np1008637

Keywords

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Funding

  1. NSF [OCE-0095724, 0550468, CHE0741968]
  2. NIH [CA122256, AI039987]
  3. Ruth L. Kirschstein National Research Service [T32 CA009523]
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [0741968] Funding Source: National Science Foundation
  6. Office of Polar Programs (OPP)
  7. Directorate For Geosciences [0550468] Funding Source: National Science Foundation

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The complete stereostructures of xestoproxamines A-C, from the Bahamian sponge Neopetrosia proxima, were assigned from spectroscopic analysis, including MS, 2D NMR, and integrated degradation-CD analysis. Two new CD application protocols are described for defining absolute configuration: one for allylic methyl groups in branched chains and a second for the heterocyclic core bis-piperidine with Specific applicability to other members of this class alkaloids-known for their stereoheterogeneity-and tertiary cyclic amines in general.

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