2. Academic Validation
  3. Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E

Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E

  • Chem Pharm Bull (Tokyo). 1995 May;43(5):777-82. doi: 10.1248/cpb.43.777.
N Saito 1,  S Harada,  M Nishida,  I Inouye,  A Kubo
Affiliations

Affiliation

  • 1 Meiji College of Pharmacy, Tokyo, Japan.
PMID: 7553964 DOI: 10.1248/cpb.43.777
Abstract

Treatment of (-)-saframycin A (1a) with selenium oxide in acetic acid afforded (-)-saframycin G (1g), and a catalytic reduction and regioselective oxidation sequence afforded the saframycin Mx type compound (3). We applied this methodology to the transformation of (+/-)-5-hydroxysaframycin B (11) to the hydroquinone (1e). Acetylation of 1e with acetic anhydride in pyridine gave the triacetate (13), which is identical with the triacetyl derivative of natural saframycin E.

Figures
Products