Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration

KELEBEKLI, Latif; Çelik, Murat; Şahin, Ertan; Kara, Yunus; BALCI, Metin

doi:10.1016/j.tetlet.2006.07.108

Makale Tam Makale Uluslararası 2006

Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration

Latif KELEBEKLI, Murat Çelik, Ertan Şahin, Yunus Kara, Metin BALCI

Tetrahedron Letters Cilt 47 · Sayı 39 · ss. 7031–7035 · 25.09.2006

DOI ile aç

Özet

A new aminocyclitol derived from bicyclo[4.2.0(1,6)]octane was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy-bicyclo[4.2.0]octa-2,4-diene afforded a bicyclic endoperoxide. Reduction of the endoperoxide with thiourea followed by a palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Oxidation of the double bond in the oxazolidinone with KNlnO(4) followed by acetylation gave the oxazolidinone-tetraacetate whose exact configuration was determined by X-ray diffraction analysis. Hydrolysis of the oxazolidinone ring and removal of the acetate groups furnished the desired aminocyclitol. (c) 2006 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

oxidation EFFICIENT Compounds cyclitols aminocyclitol endoperoxide bicyclic aliphatic X-ray analysis GLYCOSIDASE INHIBITORY-ACTIVITY RING-CLOSING METATHESIS ENANTIOMERICALLY PURE RADICAL CYCLIZATION CONDURITOL ANALOGS D-GLUCOSE CARBASUGAR POLYCYCLITOLS CARBOCYCLES

Atıf için künye

KELEBEKLI, L., Çelik, M., Şahin, E., Kara, Y., & BALCI, M. (2006). Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration. Tetrahedron Letters, 47(39), 7031–7035. https://doi.org/10.1016/j.tetlet.2006.07.108

BibTeX

@article{kelebekli2006-66681,
  author = {KELEBEKLI, Latif and Çelik, Murat and Şahin, Ertan and Kara, Yunus and BALCI, Metin},
  title = {Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration},
  journal = {Tetrahedron Letters},
  year = {2006},
  volume = {47},
  number = {39},
  pages = {7031--7035},
  issn = {0040-4039},
  doi = {10.1016/j.tetlet.2006.07.108},
  url = {https://akademik.atauni.edu.tr/yayinlar/66681-stereospecific-synthesis-of-a-new-class-of-aminocyclitol-with-the-conduramine-d}
}