An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

Lana M. Grubb; April L. Dowdy; Heather S. Blanchette; Gregory K. Friestad; Bruce P. Branchaud

doi:10.1016/S0040-4039(99)00334-2

An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

Lana M. Grubb, April L. Dowdy, Heather S. Blanchette, Gregory K. Friestad, Bruce P. Branchaud

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

21 Scopus citations

Abstract

In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation.

Original language	English (US)
Pages (from-to)	2691-2694
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(99)00334-2
State	Published - Apr 2 1999
Externally published	Yes

Keywords

Arylation
Conformation
Cyclitols
Heck Reactions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(99)00334-2

Cite this

@article{131556a20cea4826a2575d24383c29d4,

title = "An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem",

abstract = "In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation.",

keywords = "Arylation, Conformation, Cyclitols, Heck Reactions",

author = "Grubb, {Lana M.} and Dowdy, {April L.} and Blanchette, {Heather S.} and Friestad, {Gregory K.} and Branchaud, {Bruce P.}",

note = "Funding Information: Acknowledgment. This research was supported by NSF CHE-9423782, the Medical Research Foundation of Oregon and the Elsa U. Pardee Foundation for Cancer Research. The authors gratefully acknowledge Dr. Timothy Weakley for X-ray crystallographic determination of the structures of 17a and 22.",

year = "1999",

month = apr,

day = "2",

doi = "10.1016/S0040-4039(99)00334-2",

language = "English (US)",

volume = "40",

pages = "2691--2694",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - An approach to (+)-pancratistatin from D-glucose

T2 - A conformational lock solves a stereochemical problem

AU - Grubb, Lana M.

AU - Dowdy, April L.

AU - Blanchette, Heather S.

AU - Friestad, Gregory K.

AU - Branchaud, Bruce P.

N1 - Funding Information: Acknowledgment. This research was supported by NSF CHE-9423782, the Medical Research Foundation of Oregon and the Elsa U. Pardee Foundation for Cancer Research. The authors gratefully acknowledge Dr. Timothy Weakley for X-ray crystallographic determination of the structures of 17a and 22.

PY - 1999/4/2

Y1 - 1999/4/2

N2 - In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation.

AB - In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation.

KW - Arylation

KW - Conformation

KW - Cyclitols

KW - Heck Reactions

UR - http://www.scopus.com/inward/record.url?scp=0033515866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033515866&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00334-2

DO - 10.1016/S0040-4039(99)00334-2

M3 - Article

AN - SCOPUS:0033515866

SN - 0040-4039

VL - 40

SP - 2691

EP - 2694

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this