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Synthesis of a Small Repertoire of Non‐Racemic 5a‐Carbahexopyranoses and 1‐Thio‐5a‐carbahexopyranoses
Author(s) -
Zanardi Franca,
Battistini Lucia,
Marzocchi Lucia,
Acquotti Domenico,
Rassu Gloria,
Pinna Luigi,
Auzzas Luciana,
Zambrano Vincenzo,
Casiraghi Giovanni
Publication year - 2002
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 - 10.1002/1099-0690(200206)2002:12<1956::aid-ejoc1956>3.0.co;2-y
Subject(s) - chemistry , stereoselectivity , aldol reaction , stereochemistry , thio , bifunctional , bicyclic molecule , diene , organic chemistry , catalysis , natural rubber
A short and practical entry to optically pure 5a‐carbahexopyranose and 1‐thio‐5a‐carbahexopyranose representatives is described. Besides a few functional group and protecting group manipulations, the synthetic scheme counts on two fundamental carbon−carbon bond‐forming reactions, namely (i) a regio‐ and stereoselective aldol addition between heterocyclic (silyloxy)diene donors ( 6 or 13 ) and D ‐glyceraldehyde as the acceptor ( 7 ) and (ii) a chemo‐ and stereoselective silylative cycloaldolization involving bifunctional aldehydes ( 10 , 16 , and 21 ). The 1 H NMR based configurational and conformational assignment of target structures 1 − 5 and bicyclic intermediates 11 , 12 , 17 , 18 , and 22 is discussed. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)