Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Pyrrolizidine alkaloids. A concise entry to (-)-pyrrolam A.Electric Literature of C10H19NO3.
The synthesis of (-)-pyrrolam A starting from (R)-prolinol was described. The key step was the dehydrative alkylation of a conveniently protected (R)-prolinol I (R = CH2OH, R1 = CO2CMe3) with tri-Et methanetricarboxylate under the conditions of the Mitsunobu reaction to give tricarboxylate I [R = CH2C(CO2Et)3, R1 = CO2CMe3]. The tricarboxylate was converted to acid I [R = (CH2)2CO2H, R1 = H], which was cyclized to form (+)-dihydropyrrolam A (II). II was subsequently converted to (-)-pyrrolam A (III) via selenation with PhSeCl followed by oxidation with H2O2.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica