115483-04-0Relevant articles and documents
Stereoselective Synthesis of Stagonolide G from d -Mannitol
Pavan Kumar, Chebolu Naga Sesha Sai,Ravinder, Mettu,Naveen Kumar, Singam,Jayathirtha Rao, Vaidya
, p. 451 - 458 (2011/04/16)
A highly convergent, stereoselective total synthesis of a ten-membered lactone, stagonolide G, is described. Epoxide ring-opening with vinyl Grignard, Yamaguchi esterification and ring-closing metathesis are the key steps involved in the present approach.
Asymmetric total synthesis of stagonolide G
Ramesh, Dasari,Rajaram, Singanaboina,Prabhakar, Peddikotla,Ramulu, Udugu,Kumar Reddy, Dorigondla,Venkateswarlu, Yenamandra
, p. 1226 - 1233 (2011/09/14)
A simple asymmetric total synthesis of stagonolide G (1) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard reactions are involved in generating the stereogenic centers C(4) and C(8), followed by Grubbs-II-ca
Synthesis of substituted tetrahydrofuran by electrophile-induced cyclization of 4-pentene-1,2,3-triols - An example of 5-exo versus 5-endo cyclization governed by the electrophile
Bravo, Fernando,Castillon, Sergio
, p. 507 - 516 (2007/10/03)
Differently protected 4-pentene-1,2,3-triols 5-8 were obtained from glyceraldehyde and submitted to iodine-based electrophile-induced cyclization to give tetrahydrofuran derivatives 10 and 18, with high chemo-, regio-, and stereo-selectivity, through a 5-exo cyclization process. However, when an electrophilic selenium reagent was treated with similar alkene triols 5, 7, and 8, the product depended on the protecting group at the primary hydroxy moiety. Thus, while compounds 5a and 5b, unprotected at the primary hydroxy group, give compounds 26 and 27, and 32 and 33, respectively, through a 5-exo cyclization process, compounds 7 and 8, protected at the primary hydroxy group, give the 5-endo cyclization products 22-25 and 28-31 in good yields. The electrophile-induced cyclization of 4-pentene-1,2,3-triols to give tetrahydrofuran derivatives can be directed towards a 5-exo process by the use of iodine or, when the primary hydroxy group is unprotected, selenium. When the primary hydroxy group is protected, use of selenium results in 5-endo cyclization.
Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step
Bravo,Kassou,Castillon
, p. 1187 - 1190 (2007/10/03)
Differently protected erythro and threo furanoid glycals were synthesised from 4-pentene-1,2,3-triol, through selenium induced 5-endo-trig cyclization and selenoxide elimination.
