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

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

Journal article

Peer reviewed

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 and Bruce P Branchaud

Tetrahedron letters, Vol.40(14), pp.2691-2694

1999

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

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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. Graphic

Arylation

Heck Reactions

Cyclitols

Conformation

Details

Title: Subtitle: An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem
Creators: Lana M Grubb
April L Dowdy
Heather S Blanchette
Gregory K Friestad
Bruce P Branchaud
Resource Type: Journal article
Publication Details: Tetrahedron letters, Vol.40(14), pp.2691-2694
Publisher: Elsevier Ltd
DOI: 10.1016/S0040-4039(99)00334-2
ISSN: 0040-4039
eISSN: 1873-3581
Language: English
Date published: 1999
Academic Unit: Chemistry
Record Identifier: 9983985825602771

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