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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, E
Alves, CD
Bockelmann, MA
Pilli, RA
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 threestep 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
Country: Brasil
Editor: Soc Brasileira Quimica
Rights: aberto
Identifier DOI: 10.1590/S0100-40422008000400012
Date Issue: 2008
Appears in Collections:Unicamp - Artigos e Outros Documentos

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