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

Authors
Grubb, LM Dowdy, AL Blanchette, HS Friestad, GK Branchaud, BP
Citation
Lm. Grubb et al., An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem, TETRAHEDR L, 40(14), 1999, pp. 2691-2694
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
14
Year of publication
1999
Pages
2691 - 2694
Database
ISI
SICI code
0040-4039(19990402)40:14<2691:AAT(FD>2.0.ZU;2-L
Abstract
In previous work we discovered that reductive Pd-mediated aryl-enone cycliz ation of an advanced intermediate resulted in epimerization of a critical s tereocenter. Analysis of conformational and steric effects could rationaliz e the result. Based on that analysis it was anticipated that a conformation al lock could suppress the undesired epimerization. Results reported herein confirm that expectation. (C) 1999 Elsevier Science Ltd. All rights reserv ed.