Magnesiate addition/ring-expansion strategy to access the 6-7-6 tricyclic core of hetisine-type C20-diterpenoid alkaloids

Pflueger, Jason J., Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531, deGruyter, Justine N., Perea, Melecio A. and Sarpong, Richmond 2017. Magnesiate addition/ring-expansion strategy to access the 6-7-6 tricyclic core of hetisine-type C20-diterpenoid alkaloids. Organic Letters 19 (17) , pp. 4632-4635. 10.1021/acs.orglett.7b02260

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Abstract

A synthetic strategy to access the fused 6–7–6 tricyclic core of hetisine-type C20-diterpenoid alkaloids is reported. This strategy employs a Diels–Alder cycloaddition to assemble a fused bicyclic anhydride intermediate, which is elaborated to a vinyl lactone-acetal bearing an aromatic ring in five steps. Aromatic iodination is followed by magnesium–halogen exchange with a trialkyl magnesiate species, which undergoes intramolecular cyclization. Subsequent oxidation provides the desired 6–7–6 tricyclic diketoaldehyde, with carbonyl groups at all three positions for eventual C–N bond formation and subsequent elaboration.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	ACS
ISSN:	1523-7060
Date of First Compliant Deposit:	31 August 2017
Date of Acceptance:	15 August 2017
Last Modified:	17 Nov 2024 04:45
URI:	https://orca.cardiff.ac.uk/id/eprint/104180

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