86227-43-2Relevant articles and documents
Isobenzofurans as Synthetic Intermediates: Synthesis and Biological Activity of 8-epi-(–)-Ajudazol B
Adair, Liam,Egan, Ben A.,Pearson, Colin M.,Lopez-Gonzalez, Ricardo,Kuchar, Michal,Mendoza-Mendoza, Artemio,Prunet, Jo?lle,Marquez, Rodolfo
supporting information, p. 6661 - 6672 (2020/10/15)
Ajudazol B is a polyketide secondary metabolite, isolated from the myxobacterium Chondromyces crocatus, that exhibits potent biological activity. Herein, we report a convergent total synthesis of 8-epi-(–)-ajudazol B. The key step is a regio-selective alk
Syn-effect' in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones
Jiménez, Jacqueline,Ramírez, Juáncarlos,Huelgas, Gabriela,Meléndrez, Ruth,Cabrera-Vivas, Blanca M.,Sansinenea, Estibaliz,Ortiz, Aurelio
, p. 4590 - 4597 (2015/06/08)
Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O.
Diastereoselective alkylations of oxazolidinone vinylogous glycolates
Jiménez, Jacqueline,Meza-León, Rosa L.,Sartillo-Piscil, Fernando,Meléndez, Francisco J.,Sansinenea, Estibaliz,Ortiz, Aurelio
, p. 4775 - 4778 (2012/09/08)
A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the γ-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds.
BIFUNCTIONAL CHIRAL SYNTHONS VIA BIOCHEMICAL METHODS. VI. C5 ISOPRENOID UNITS.
VanMiddlesworth, Frank,Wang, Yi Fong,Zhou, Bing-nan,DiTullio, Dennis,Sih, C. J.
, p. 961 - 964 (2007/10/02)
Two methods for the preparation of the isoprenoid chiron 4 have been developed using a microbial kinetic resolution of 5 and an enantiotopically selective hydrolysis of 7 catalyzed by PLE.
