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

Journal Article


Abstract


  • 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.

UOW Authors


  •   Thaima, Thanaphat (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2019

Citation


  • Thaima, T., Willis, A. C. & Pyne, S. G. (2019). Progress toward the total synthesis of 9β-hydroxyvertine: Construction of an advanced quinolizidine intermediate. Tetrahedron, 75 (36), 130476-1-130476-24.

Scopus Eid


  • 2-s2.0-85069976645

Start Page


  • 130476-1

End Page


  • 130476-24

Volume


  • 75

Issue


  • 36

Place Of Publication


  • United Kingdom

Abstract


  • 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.

UOW Authors


  •   Thaima, Thanaphat (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2019

Citation


  • Thaima, T., Willis, A. C. & Pyne, S. G. (2019). Progress toward the total synthesis of 9β-hydroxyvertine: Construction of an advanced quinolizidine intermediate. Tetrahedron, 75 (36), 130476-1-130476-24.

Scopus Eid


  • 2-s2.0-85069976645

Start Page


  • 130476-1

End Page


  • 130476-24

Volume


  • 75

Issue


  • 36

Place Of Publication


  • United Kingdom