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

TETRAHEDRON

卷:75

Article

Thaima, Thanaphat¹  Willis, Anthony C.²  Pyne, Stephen G.¹ 

[1] Univ Wollongong, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia

[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

关键词: 9 beta-hydroxyvertine;    Petasis borono-Mannich reaction;    Quinolizidine;    Biphenyl;    Rotamers;   

DOI  :  10.1016/j.tet.2019.130476

来源: Elsevier

【 摘 要 】

Progress toward the total synthesis of 9 beta-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. (C) 2019 Elsevier Ltd. All rights reserved.

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