A chiral pool approach toward the synthesis of thalidomide metabolites

Frederick A. Luzzio; Damien Y. Duveau; William D. Figg

doi:10.3987/com-06-s(w)28

A chiral pool approach toward the synthesis of thalidomide metabolites

Frederick A. Luzzio^*, Damien Y. Duveau, William D. Figg

^*Corresponding author for this work

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

6 Scopus citations

Abstract

A synthetic strategy toward the glutarimide-derived metabolite of thalidomide, 5′-hydroxythalidomide (5′-OH THD, 2) was developed which utilizes aspartic acid as a "chiral pool"-type starting material. The synthesis incorporates a Henry reaction as the key carbon-carbon bond-forming step followed by a tandem reduction-cyclization of the intermediate nitroalcohol in forming the heterocyclic core of 5′-OH THD.

Original language	English
Pages (from-to)	321-334
Number of pages	14
Journal	Heterocycles
Volume	70
DOIs	https://doi.org/10.3987/com-06-s(w)28
State	Published - 31 Dec 2006
Externally published	Yes

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title = "A chiral pool approach toward the synthesis of thalidomide metabolites",

abstract = "A synthetic strategy toward the glutarimide-derived metabolite of thalidomide, 5′-hydroxythalidomide (5′-OH THD, 2) was developed which utilizes aspartic acid as a {"}chiral pool{"}-type starting material. The synthesis incorporates a Henry reaction as the key carbon-carbon bond-forming step followed by a tandem reduction-cyclization of the intermediate nitroalcohol in forming the heterocyclic core of 5′-OH THD.",

author = "Luzzio, {Frederick A.} and Duveau, {Damien Y.} and Figg, {William D.}",

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AU - Luzzio, Frederick A.

AU - Duveau, Damien Y.

AU - Figg, William D.

PY - 2006/12/31

Y1 - 2006/12/31

N2 - A synthetic strategy toward the glutarimide-derived metabolite of thalidomide, 5′-hydroxythalidomide (5′-OH THD, 2) was developed which utilizes aspartic acid as a "chiral pool"-type starting material. The synthesis incorporates a Henry reaction as the key carbon-carbon bond-forming step followed by a tandem reduction-cyclization of the intermediate nitroalcohol in forming the heterocyclic core of 5′-OH THD.

AB - A synthetic strategy toward the glutarimide-derived metabolite of thalidomide, 5′-hydroxythalidomide (5′-OH THD, 2) was developed which utilizes aspartic acid as a "chiral pool"-type starting material. The synthesis incorporates a Henry reaction as the key carbon-carbon bond-forming step followed by a tandem reduction-cyclization of the intermediate nitroalcohol in forming the heterocyclic core of 5′-OH THD.

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U2 - 10.3987/com-06-s(w)28

DO - 10.3987/com-06-s(w)28

M3 - Article

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SN - 0385-5414

VL - 70

SP - 321

EP - 334

JO - Heterocycles

JF - Heterocycles

ER -

A chiral pool approach toward the synthesis of thalidomide metabolites

Abstract

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