Abstract
The enantioselective synthesis (3.7% overall yield in nine steps from 2) and biological screening of the ethyl analog of the macrocyclic marine alkaloid haliclorensin C (compound 5) are reported. Amino alcohol 3, generated by a LiNH2BH3-promoted reductive ring-opening/debenzylation sequence from phenylglycinol-derived lactam 2, was used as the starting chiral linear building block. Incorporation of the undecene chain via the nosyl derivative 12, methylenation of the pentanol moiety, and a ring-closing metathesis are the key steps of the synthesis.
Highlights
Haliclorensin C (1) is a minor marine alkaloid isolated from the sponge Haliclona tulearensis collected in January 2006 in Salary Bay, Madagascar [1]
Www.mdpi.com/journal/molecules comparison of the 1H- and 13C-NMR spectra of both the base and hydrochloride of the synthetic product with the spectra reported for the natural product revealed that the isolated sample of haliclorensin C corresponded to a protonated sample
In recent years we have reported preparation of enantiopure five-carbon linear building
Summary
Haliclorensin C (1) is a minor marine alkaloid isolated from the sponge Haliclona tulearensis collected in January 2006 in Salary Bay, Madagascar [1]. 24, 1069; structure doi:10.3390/molecules24061069 www.mdpi.com/journal/molecules comparison of the 1H- and 13C-NMR spectra of both the base and hydrochloride of the synthetic product with the spectra reported for the natural product revealed that the isolated sample of haliclorensin C corresponded to a protonated sample. In recent we have reported the preparation of enantiopure building to blocks blocks from years phenylglycinol-derived bicyclic lactam scaffolds five-carbon and theirlinear application the from phenylglycinol-derived bicyclic scaffolds and their application to the enantioselective total enantioselective total synthesis of lactam macrocyclic natural products, such as haliclorensin marine synthesis macrocyclic natural products, such as haliclorensin marine alkaloids [6], fluvirucinin [7],3alkaloidsof[6], fluvirucinin.
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