Regioselective cleavage of rings E and F in sarsasapogenin

Sapogenins from the 25R and 25S series show a marked difference on the E/F regioselectivity of the spiroketal cleavage with BF3/Ac2O

Jesús Sandoval-Ramı́rez

2003

Scholarcy highlights

  • Sapogenins from the 25R and 25S series show a marked difference on the E/F regioselectivity of the spiroketal cleavage with BF3/Ac2O
  • The lower E/F selectivity in the cleavage of 1 is attributed to steric hindrance resulting from the axial methyl in F ring on a β elimination forming the dihydropyran double bond in the major product 8

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