An alternative total synthesis of solamargine

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Solamargine,(25R)-3-{O-L-rhamnopyranosyl-(1 2)-[O-L-rhamnopyranosyl-(1 4)]-D-glucopyranosyloxy}-22-Nspirosol-5-ene,isolated from the berries of solanum aculeastrum,has been synthesized in 26.8% overall yield.First glycosylation before N-cyclization significantly facilitated synthesis of the desired molecule.We anticipate that this work will provide a new approach to access solamargine and its diversified analogues. Solamargine, (25R) -3- {OL- rhamnopyranosyl- (1 2) - [OL- rhamnopyranosyl- (1 4)] - D-glucopyranosyloxy} -22- Nspirosol- 5-ene, isolated from the berries of solanum aculeastrum, has been synthesized in 26.8% overall yield. First glycosylation before N-cyclization significantly facilitated synthesis of the desired molecule. We anticipate that this work will provide a new approach to access solamargine and its diversified analogues.
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