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

Thanaphat Thaima; Anthony C. Willis; Stephen G. Pyne

doi:10.1016/j.tet.2019.130476

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

Thanaphat Thaima, Anthony C. Willis, Stephen G. Pyne^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Article number	130476
Journal	Tetrahedron
Volume	75
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2019.130476
Publication status	Published - 6 Sept 2019

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10.1016/j.tet.2019.130476

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

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.",

keywords = "9β-hydroxyvertine, Biphenyl, Petasis borono-Mannich reaction, Quinolizidine, Rotamers",

author = "Thanaphat Thaima and Willis, {Anthony C.} and Pyne, {Stephen G.}",

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T2 - Construction of an advanced quinolizidine intermediate

AU - Thaima, Thanaphat

AU - Willis, Anthony C.

AU - Pyne, Stephen G.

PY - 2019/9/6

Y1 - 2019/9/6

N2 - 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.

AB - 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.

KW - 9β-hydroxyvertine

KW - Biphenyl

KW - Petasis borono-Mannich reaction

KW - Quinolizidine

KW - Rotamers

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DO - 10.1016/j.tet.2019.130476

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VL - 75

JO - Tetrahedron

JF - Tetrahedron

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M1 - 130476

ER -

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

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