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

Funding

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.).

Funders	Funder number
Eli Lilly and Co.
U.S. Dept. of Education
Author National Science Foundation National Science Foundation National Institutes of Health National Institutes of Health National Institutes of Health National Institutes of Health National Science Foundation National Science Foundation	CHE 8806805, CHE-9423782

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(97)01325-7

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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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doi = "10.1016/S0040-4039(97)01325-7",

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journal = "Tetrahedron Letters",

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

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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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JO - Tetrahedron Letters

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IS - 34

ER -

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

Abstract

Funding

ASJC Scopus subject areas

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