An efficient regioselective and diastereoselective synthesis of the epoxy-quinol functionality as building block for the manumycin antibiotics by the sequence of photooxygenation, reduction and Weitz-Scheffer epoxidation

Adam, W; Kılıç, Hamdullah; Saha-Moller, Cr

Makale Tam Makale Uluslararası 2002

An efficient regioselective and diastereoselective synthesis of the epoxy-quinol functionality as building block for the manumycin antibiotics by the sequence of photooxygenation, reduction and Weitz-Scheffer epoxidation

Synlett Sayı 3 · ss. 510–512 · 01.03.2002

Özet

The photooxygenation of the acetanilide 2 affords the hydroperoxide 3, which by titanium-tetraisopropoxide-catalyzed reduction with dimethyl sulfide gives the corresponding quinol 4. Regioselective and diastereoselective Weitz-Scheffer epoxidation of the latter by tert-butyl hydroperoxide (TBHP) and DBU as base catalyst leads to the cis-epoxy quinol 1, the essential functionality in Manumycin antibiotics.

Anahtar kelimeler

ANALOGS biosynthesis Regioselectivity PHOTOOXYGENATION FAMILY quinol Weitz-Scheffer epoxidation diastercoselectivity LL-C10037-ALPHA

Atıf için künye

Adam, W., Kılıç, H., & Saha-Moller, C. (2002). An efficient regioselective and diastereoselective synthesis of the epoxy-quinol functionality as building block for the manumycin antibiotics by the sequence of photooxygenation, reduction and Weitz-Scheffer epoxidation. Synlett(3), 510–512.

BibTeX

@article{adam2002-71186,
  author = {Adam, W and Kılıç, Hamdullah and Saha-Moller, Cr},
  title = {An efficient regioselective and diastereoselective synthesis of the epoxy-quinol functionality as building block for the manumycin antibiotics by the sequence of photooxygenation, reduction and Weitz-Scheffer epoxidation},
  journal = {Synlett},
  year = {2002},
  number = {3},
  pages = {510--512},
  issn = {0936-5214},
  url = {https://akademik.atauni.edu.tr/yayinlar/71186-an-efficient-regioselective-and-diastereoselective-synthesis-of-the-epoxy-quinol}
}