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. (author)
Pereira, Elaine;
Alves, Conceicao de Fatima;
Boeckelmann, Maria Alice;
Pilli, Ronaldo A
[1]
- Universidade Estadual de Campinas (UNICAMP), Campinas, SP (Brazil). Inst. de Quimica
Citation Formats
Pereira, Elaine, Alves, Conceicao de Fatima, Boeckelmann, Maria Alice, and Pilli, Ronaldo A.
Stereoselective syntheses of (+)- isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium (IV) enolates to cyclic n-acyliminium ions.
Brazil: N. p.,
2008.
Web.
Pereira, Elaine, Alves, Conceicao de Fatima, Boeckelmann, Maria Alice, & Pilli, Ronaldo A.
Stereoselective syntheses of (+)- isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium (IV) enolates to cyclic n-acyliminium ions.
Brazil.
Pereira, Elaine, Alves, Conceicao de Fatima, Boeckelmann, Maria Alice, and Pilli, Ronaldo A.
2008.
"Stereoselective syntheses of (+)- isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium (IV) enolates to cyclic n-acyliminium ions."
Brazil.
@misc{etde_21068684,
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, Conceicao de Fatima, Boeckelmann, Maria Alice, and Pilli, Ronaldo A}
abstractNote = {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. (author)}
journal = []
issue = {4}
volume = {31}
place = {Brazil}
year = {2008}
month = {Jul}
}
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, Conceicao de Fatima, Boeckelmann, Maria Alice, and Pilli, Ronaldo A}
abstractNote = {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. (author)}
journal = []
issue = {4}
volume = {31}
place = {Brazil}
year = {2008}
month = {Jul}
}