Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate
Özet
A method for preparing haloconduritols having a conduritol-A construction is described. A mixture of endo- and exo-cycloadduct derivatives prepared from the Diels-Alder reaction of furan and vinylene carbonate was converted into diacetate derivatives by hydrolysis (K2CO3/MeOH) followed by acetylation (Ac2O/Pyridine). Boron trihalide (BBr3 or BCl3)-assisted ring-opening of the endo-diacetate in CH2O2 at -78degreesC gave (1alpha,2alpha,30,6beta)-6-halogeno-4-cyclohexene-1,2,3-triol 1,2-diacetate from which the corresponding triacetate was prepared by acetylation (AcCl). trans-Esterification of the triacetate (MeOH/HCl) afforded (1alpha,2alpha,3beta,6beta)-6-halogeno-4-cyclohexene-1,2,3-triol (X=Br or Cl). BF3-Assisted ring-opening of the endo-diacetate in CH2O2 gave (1alpha,2alpha,3beta,6beta)-6-chloro-4-cyclohexene-1,2,3-triol 1,2-diacetate by means of halogen exchange. (C) 2003 Elsevier Science Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
BARAN, A., Kazaz, C., Seçen, H., & SUTBEYAZ, Y. (2003). Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate. TETRAHEDRON, 59(20), 3643–3648. https://doi.org/10.1016/s0040-4020%2803%2900510-6
BibTeX
@article{baran2003-70860,
author = {BARAN, Arif and Kazaz, Cavit and Seçen, Hasan and SUTBEYAZ, Yaşar},
title = {Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate},
journal = {TETRAHEDRON},
year = {2003},
volume = {59},
number = {20},
pages = {3643--3648},
issn = {0040-4020},
doi = {10.1016/s0040-4020(03)00510-6},
url = {https://akademik.atauni.edu.tr/yayinlar/70860-synthesis-of-haloconduritols-from-an-endo-cycloadduct-of-furan-and-vinylene}
}