A synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide.
| cam.depositDate | 2022-04-14 | |
| cam.issuedOnline | 2022-05-10 | |
| cam.orpheus.success | 2022-04-14 - Embargo set during processing via Fast-track | |
| dc.contributor.author | Stockdale, Tegan P | |
| dc.contributor.author | Lam, Nelson YS | |
| dc.contributor.author | Paterson, Ian | |
| dc.contributor.orcid | Lam, Nelson YS [0000-0002-9307-0619] | |
| dc.contributor.orcid | Paterson, Ian [0000-0002-8861-9136] | |
| dc.date.accessioned | 2022-04-14T23:30:56Z | |
| dc.date.available | 2022-04-14T23:30:56Z | |
| dc.date.issued | 2022-05-10 | |
| dc.date.updated | 2022-04-14T11:01:23Z | |
| dc.description.abstract | 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. | |
| dc.identifier.doi | 10.17863/CAM.83547 | |
| dc.identifier.eissn | 1364-548X | |
| dc.identifier.issn | 1359-7345 | |
| dc.identifier.uri | https://www.repository.cam.ac.uk/handle/1810/336122 | |
| dc.publisher | Royal Society of Chemistry (RSC) | |
| dc.publisher.department | Trinity Hall | |
| dc.publisher.department | Department of Chemistry | |
| dc.publisher.url | http://dx.doi.org/10.1039/d2cc01802k | |
| dc.rights | Attribution 4.0 International | |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
| dc.subject | Antineoplastic Agents | |
| dc.subject | Magnetic Resonance Spectroscopy | |
| dc.subject | Polyketides | |
| dc.subject | Stereoisomerism | |
| dc.title | A synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide. | |
| dc.type | Article | |
| prism.publicationName | Chem Commun (Camb) | |
| pubs.licence-display-name | Apollo Repository Deposit Licence Agreement | |
| pubs.licence-identifier | apollo-deposit-licence-2-1 | |
| rioxxterms.type | Journal Article/Review | |
| rioxxterms.version | AM | |
| rioxxterms.versionofrecord | 10.1039/d2cc01802k |
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