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Type: Artigo de periódico
Title: Stereoselective syntheses of (+)- isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium (iv) enolates to cyclic n-acyliminium ions
Author: Pereira, Elaine
Alves, Conceição de Fátima
Böckelmann, Maria Alice
Pilli, Ronaldo A.
Abstract: The stereoselective addition of the titanium (IV) enolates derived from (S)-4-isopropyl-N-4-chlorobutyryl-1,3-thiazolidine-2-thione (8) and from (S)-4-isopropyl-N-4-chloropentanoyl-1,3-thiazolidine-2-thione (9) to N-Boc-2-methoxypyrrolidine (5b) afforded the addition products (+)-10 and (+)-11 in 84% yield in both cases, as 8.6:1 and 10:1 diastereoisomeric mixtures, respectively. A three-step sequence allowed to convert these adducts to (+)-isoretronecanol (1) and (+)-5-epi-tashiromine (2) in 43% and 49% overall yield, respectively.
Subject: (+)-isoretronecanol
asymmetric synthesis
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0100-40422008000400012
Date Issue: 1-Jan-2008
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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