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Total Synthesis of Natural Hyacinthacine C-5 and Six Related Hyacinthacine C-5 Epimers

Carroll, Anthony W; Savaspun, Kongdech; Willis, Anthony; Hoshino, Masako; Kato, Atsushi; Pyne, Stephen G

Description

The total synthesis of natural (+)-hyacinthacine C-5 was achieved, which allowed correction of its initially proposed structure, as well as six additional hyacinthacine C-type compounds. These compounds were readily accessible from two epimeric anti-1,2-amino alcohols. Keeping a common A-ring configuration, chemical manipulation occurred selectively on the B-ring of the hyacinthacine C-type products through methods of syn-dihydroxylation, S(N)2 ring-opening of a cyclic sulfate, and also...[Show more]

CollectionsANU Research Publications
Date published: 2018
Type: Journal article
URI: http://hdl.handle.net/1885/160514
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.8b00585

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