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Progress toward the total synthesis of 9β-hydroxyvertine: Construction of an advanced quinolizidine intermediate

Thaima, Thanaphat; Willis, Anthony; Pyne, Stephen G

Description

Progress toward the total synthesis of 9β-hydroxyvertine 2 is described. Our approach involves a Petasis borono-Mannich reaction to assemble a key intermediate A, securing the correct configuration at H-9 and H-10 in the final targeted molecule. Subsequent formation of the quinolizidine framework B allowed the synthesis of an advanced intermediate containing all but the lactone moiety of 2. Our unsuccessful attempts at introducing this lactone feature are also described.

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
URI: http://hdl.handle.net/1885/210570
Source: Tetrahedron
DOI: 10.1016/j.tet.2019.130476

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