A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Gregory K. Friestad; Bruce P. Branchaud

doi:10.1016/S0040-4039(97)01325-7

A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Gregory K. Friestad, Bruce P. Branchaud

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

16 Scopus citations

Abstract

A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.

Original language	English (US)
Pages (from-to)	5933-5936
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(97)01325-7
State	Published - Aug 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations",

abstract = "A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.",

author = "Friestad, {Gregory K.} and Branchaud, {Bruce P.}",

note = "Funding Information: AcknowledgmentT. his research was supported by NSF CHE 8806805, NSF CHE-9423782, Eli Lilly and Co., and a fellowship from the U.S. Dept. of Education Graduate Assistance in Areas of National Need Program (G. K. F.).",

year = "1997",

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T1 - A new approach to the pancratistatin C-ring from D-Glucose

T2 - Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

AU - Friestad, Gregory K.

AU - Branchaud, Bruce P.

N1 - Funding Information: AcknowledgmentT. his research was supported by NSF CHE 8806805, NSF CHE-9423782, Eli Lilly and Co., and a fellowship from the U.S. Dept. of Education Graduate Assistance in Areas of National Need Program (G. K. F.).

PY - 1997/8

Y1 - 1997/8

N2 - A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.

AB - A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.

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A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Abstract

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