An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

BARAN, Arif; Seçen, Hasan; BALCI, Metin

doi:10.1055/s-2003-40517

Makale Tam Makale Uluslararası 2003

An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

Arif BARAN, Hasan Seçen, Metin BALCI

Synthesis (Germany) Sayı 10 · ss. 1500–1502 · 01.07.2003

DOI ile aç

Özet

gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aalpha,5alpha,7aalpha)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole. cis-Hydroxylation of the benzodioxole followed by acetylation with AcCl gave 5-O-methyl-gala-quercitol tetraacetate from which gala-quercitol was obtained by hydrolysis and demethylation with aq HBr (47%).

Atıf için künye

BARAN, A., Seçen, H., & BALCI, M. (2003). An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene. Synthesis (Germany)(10), 1500–1502. https://doi.org/10.1055/s-2003-40517

BibTeX

@article{baran2003-71399,
  author = {BARAN, Arif and Seçen, Hasan and BALCI, Metin},
  title = {An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene},
  journal = {Synthesis (Germany)},
  year = {2003},
  number = {10},
  pages = {1500--1502},
  issn = {0039-7881},
  doi = {10.1055/s-2003-40517},
  url = {https://akademik.atauni.edu.tr/yayinlar/71399-an-efficient-and-highly-stereoselective-synthesis-of-gala-quercitol-from-14}
}