Premium
Nucleophilic Additions to Cyclic Nitrones en Route to Iminocyclitols – Total Syntheses of DMDP, 6‐deoxy‐DMDP, DAB‐1, CYB‐3, Nectrisine, and Radicamine B
Author(s) -
Merino Pedro,
Delso Ignacio,
Tejero Tomás,
Cardona Francesca,
Marradi Marco,
Faggi Enrico,
Parmeggiani Camilla,
Goti Andrea
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800098
Subject(s) - chemistry , stereocenter , stereochemistry , nucleophilic addition , hydroxymethyl , reagent , nucleophile , yield (engineering) , enantioselective synthesis , organic chemistry , materials science , metallurgy , catalysis
Abstract Highly diastereoselective nucleophilic additions to cyclic nitrones derived from L ‐malic acid and D ‐arabinose have been used for the construction of enantiomerically pure polyhydroxylated pyrrolidines. The synthetic strategy adopted was based on an oxidation/reduction protocol involving hydroxylamine/nitrone pairs and demonstrates the use of reagent‐ and substrate‐derived stereocontrol. In most cases reactions took place with total diastereoselectivity and in quantitative yield, with no purification being necessary. By this strategy, 2‐(hydroxymethyl)‐, 2‐(aminomethyl)‐, and 2‐aryl‐substituted polyhydroxylated pyrrolidines have been prepared with abundant configurational diversity. The use of appropriate substrates and reagents allowed for approaches to DMDP, 6‐deoxy‐DMDP, DAB‐1, CYB‐3, nectrisine and radicamine B. Several analogues of these compounds with inverted configuration at one or more stereocenters were also prepared.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)