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.