The Synthesis of (25R)-22αN-[15ξ,17α-²H₂]-Spirosol-5-en-3β-ol ([15ξ,17α-²H₂] Solasodine) and Assignment of the ¹³C N.M.R. Spectra of Solasodine and its Derivatives

Abstract

(25R)-22αN-[15ζ,17α-²H₂]Spirosol-5-en-3β-ol ([15ζ,17α-²H₂]solasodine) has been synthesized from solasodine and used to make unambiguous assignments of the resonance signals for C13, C14, C15, C17 and C20 in the ¹³C N.M.R. spectrum of solasodine. The complete assignments of the ¹³C N.M.R. spectra of solasodine and some of its derivatives are based on this, on paramagnetic broadening of signals due to C22, C23, C25 and C26, and on chemical shift considerations.