A synthesis-enabled relative stereochemical assignment of the C1-C28 region of hemicalide.
Publication Date
2018-03-27Journal Title
Chem Commun (Camb)
ISSN
1359-7345
Publisher
Royal Society of Chemistry (RSC)
Volume
54
Issue
26
Pages
3247-3250
Language
eng
Type
Article
This Version
VoR
Physical Medium
Print
Metadata
Show full item recordCitation
Han, B. Y., Lam, N., MacGregor, C. I., Goodman, J., & Paterson, I. (2018). A synthesis-enabled relative stereochemical assignment of the C1-C28 region of hemicalide.. Chem Commun (Camb), 54 (26), 3247-3250. https://doi.org/10.1039/c8cc00933c
Abstract
Through synthesising both candidate diastereomers of a model C1-C28 fragment of the potent cytotoxic marine polyketide hemicalide, an assignment of the relative configuration between the C1-C15 and C16-C26 regions has been achieved. By detailed NMR comparisons with the natural product, the relative stereochemistry between these two 1,6-related stereoclusters is elucidated as 13,18-syn rather than the previously proposed 13,18-anti relationship. A flexible and modular strategy using an advanced C1-C28 ketone fragment 22 is outlined to elucidate the remaining stereochemical features and achieve a total synthesis.
Embargo Lift Date
2100-01-01
Identifiers
External DOI: https://doi.org/10.1039/c8cc00933c
This record's URL: https://www.repository.cam.ac.uk/handle/1810/275443
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