A synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide.
Stockdale, Tegan P
Chem Commun (Camb)
Royal Society of Chemistry (RSC)
MetadataShow full item record
Stockdale, T. P., Lam, N. Y., & Paterson, I. (2022). A synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide.. Chem Commun (Camb) https://doi.org/10.1039/d2cc01802k
With 21 unknown stereocentres embedded in spatially separated stereoclusters, the cytotoxic polyketide hemicalide represents a seemingly intractible structural assignment problem. Herein, through the targeted synthesis of configurationally defined fragments, as well as "encoded" mixtures of diastereomers, the stereochemical elucidation of the C31-C46 region of hemicalide is achieved. Detailed NMR spectroscopic analysis of candidate fragments and comparison with the related hemicalide data strongly supported a 31,32-syn, 32,36-anti and 42,46-anti relationship. In combination with previous work on hemicalide, this reduces the number of possible structural permutations down to a more manageable eight diastereomers.
Antineoplastic Agents, Magnetic Resonance Spectroscopy, Polyketides, Stereoisomerism
Embargo Lift Date
External DOI: https://doi.org/10.1039/d2cc01802k
This record's URL: https://www.repository.cam.ac.uk/handle/1810/336122
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/
Recommended or similar items
The current recommendation prototype on the Apollo Repository will be turned off on 03 February 2023. Although the pilot has been fruitful for both parties, the service provider IKVA is focusing on horizon scanning products and so the recommender service can no longer be supported. We recognise the importance of recommender services in supporting research discovery and are evaluating offerings from other service providers. If you would like to offer feedback on this decision please contact us on: email@example.com