Title

Studies towards the synthesis of polyhydroxylated pyrrolidine alkaloids isolated from Broussonetia kazinoki (moraceae)

Publication Name

Tetrahedron

Abstract

The syntheses of L-AB1, L-DMDP, and the novel compounds, (−)-phenethyl-L-AB1, (−)-10′-deoxobroussonetine C, (−)-10′-deoxobroussonetine E, (−)-1′-epi-10′-deoxobroussonetine E, and (−)-(6S)-12′-hydroxydodecylmoranoline are reported. These syntheses start from D-xylose employing the Petasis borono-Mannich reaction to stereoselectively introduce the amino group, followed by a chemo- and regioselective O-mesylation to deliver the fully functionalized pyrrolidine moiety after intramolecular SN2-cyclisation. The synthesis of the latter targeted compound involved a ring expansion process of a prolinol moiety to a piperidine derivative under Mitsunobu reaction conditions. An attempted synthesis of desired ent-broussonetine C was unsuccesful due to formation of an unexpected tetrahydrofuran derivative in the final stage of the synthesis. The glycosidase inhibitory activities of four of the new target compounds against a panel of ten glycosidaes is also presented.

Open Access Status

This publication is not available as open access

Volume

128

Article Number

133104

Funding Number

DP130101968

Funding Sponsor

Australian Research Council

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Link to publisher version (DOI)

http://dx.doi.org/10.1016/j.tet.2022.133104