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Toward the total synthesis of patellazole B: synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton.

cam.issuedOnline2018
dc.contributor.authorPhillips, Andrew W
dc.contributor.authorAnketell, Matthew J
dc.contributor.authorBalan, Tudor
dc.contributor.authorLam, Nelson YS
dc.contributor.authorWilliams, Simon
dc.contributor.authorPaterson, Ian
dc.contributor.orcidAnketell, Matthew [0000-0002-5347-5320]
dc.contributor.orcidLam, Nelson [0000-0002-9307-0619]
dc.contributor.orcidPaterson, Ian [0000-0002-8861-9136]
dc.date.accessioned2018-11-16T00:31:18Z
dc.date.available2018-11-16T00:31:18Z
dc.date.issued2018-09-26
dc.description.abstractThe patellazoles are a family of complex marine macrolides that exhibit potent cytotoxicity against cancer cell lines. However, despite extensive characterisation efforts, their full stereochemical assignment has remained elusive. We report our approach towards the synthesis-enabled structural elucidation of patellazole B (4), a 24-membered macrolide with 16 stereocentres and a signature thiazole-containing side chain. Our plan hinges upon isolating the unknown stereocentres into a single C20-C25 fragment to facilitate the flexible assembly of various possible diastereomers of an advanced C1-C25 fragment. Towards this end, a highly convergent and modular synthesis of one candidate diastereomer 37, corresponding to the patellazole B macrocyclic skeleton, has been achieved based on the strategic application of stereocontrolled aldol methodology, combined with Suzuki and Heck cross-coupling reactions.
dc.format.mediumPrint
dc.identifier.doi10.17863/CAM.32520
dc.identifier.eissn1477-0539
dc.identifier.issn1477-0520
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/285150
dc.languageeng
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.publisher.urlhttp://dx.doi.org/10.1039/c8ob01621f
dc.subject0305 Organic Chemistry
dc.titleToward the total synthesis of patellazole B: synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton.
dc.typeArticle
dcterms.dateAccepted2018-09-06
prism.endingPage8291
prism.issueIdentifier37
prism.publicationDate2018
prism.publicationNameOrg Biomol Chem
prism.startingPage8286
prism.volume16
rioxxterms.licenseref.startdate2018-09
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserved
rioxxterms.typeJournal Article/Review
rioxxterms.versionAM
rioxxterms.versionofrecord10.1039/c8ob01621f

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