80581-23-3

Upstream product

• 80581-19-7 ((2S,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol 
• 3173-56-6 benzyl isothiocyanate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 64520-58-7 ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 79060-23-4 (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 318489-44-0 Benzyl-carbamic acid (2S,3R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethyl ester 

Downstream Products

• 317855-12-2 (4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one 
• 317855-33-7 (4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 317855-09-7 (4R)-3-benzyl-4-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated pyrrolizidine alkaloids of the alexine family by tandem ring-closing metathesis-transannular cyclization. (+)-Australine

Dienes 23 and 54, prepared from epoxy alcohol 9 via oxazolidinones 15 and 51, respectively, underwent ring-closing metathesis with Grubbs's catalyst to give azacyclooctenes 26 and 55. Treatment of each azacyclooctene with m-chloroperoxybenzoic acid afforded β-epoxide 28 from 26 and α-epoxide 61 from 60. Basic hydrolysis of each of these oxazolidinones was accompanied by transannular attack at the epoxide by nitrogen, resulting in 2-(O-benzyl)-7-deoxyalexine (29) and 1,2-di-(O-benzyl)australine (62). The latter was converted to the alkaloid australine (3) upon hydrogenolysis. Attempts to effect ring-closing metathesis of dienes 37, 38, and 46 were unsuccessful, suggesting that, while one allylic oxygen substituent can be tolerated by Grubbs's catalyst, two cannot.