New Stephaoxocane Alkaloids from <i>Stephania longa</i>

Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

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Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Kutateladze

Krenske

Williams

2019

Angewandte Chemie

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Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

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Structural misassignments of natural products are prevalent in the literature.Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance,s uch that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is astrategy for predicting the isolabilities of oxygen-substituted bridgehead natural products based on calculations of olefin strain energies,N MR chemical shifts and coupling constants (DU8 +). This approachp rovides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

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New Stephaoxocane Alkaloids from Stephania longa

Zhang

Yue

2006

ChemInform

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Three new stephaoxocane-type alkaloids, stephalonganines A -C (1 -3), together with the known eletefine (4), were isolated from the whole plant of Stephania longa. Their structures were fully characterized spectroscopically, and the absolute configurations of the new alkaloids were assigned by comparison of their circular-dichroism (CD) data with those of 1,2-dihydrostephaoxocanine (5), in combination with 2D-NMR experiments.

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New Stephaoxocane Alkaloids from Stephania longa

Cited by 10 publications

References 13 publications

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

New Stephaoxocane Alkaloids from Stephania longa

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