Total synthesis of the Z-isomers of the proposed and revised structures of aspergillide B via an iodocyclization and ring-closing metathesis strategy

Mohapatra, Debendra, Pradhan, Tapas ORCID: https://orcid.org/0000-0003-1480-7799 and Das, Pragna 2014. Total synthesis of the Z-isomers of the proposed and revised structures of aspergillide B via an iodocyclization and ring-closing metathesis strategy. Synthesis: Journal of Synthetic Organic Chemistry 46 (09) , pp. 1177-1184. 10.1055/s-0033-1340853

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Abstract

The synthesis of Z-isomers of both the proposed and revised structures of aspergillide B is described. A divergent route is employed that involves kinetically controlled ring-closing metathesis for the construction of a 14-membered macrocyclic ring, ester formation under Yamaguchi conditions, a Wacker-type oxidative cyclization for creation of the C4 stereogenic center and a previously reported diastereoselective isomerization–iodocyclization strategy for the construction of the 2,6-trans-disubstituted tetrahydropyran subunit.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Thieme Gruppe
ISSN:	0039-7881
Date of Acceptance:	3 February 2014
Last Modified:	16 May 2024 01:40
URI:	https://orca.cardiff.ac.uk/id/eprint/165585

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