954148-45-9

Upstream product

• 954148-44-8 N-[3-((1R,6S)-6-benzyloxymethyl-1-triisopropylsilanyloxymethyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide 
• 98516-10-0 acetic acid (1R,6S)-6-hydroxymethyl-cyclohex-3-enylmethyl ester 
• 954148-36-8 (1R,2S)-[2-[(acetyloxy)methyl]cyclohex-4-en-1-yl]methyl acetate 
• 954148-37-9 ((1R,6S)-6-benzyloxymethyl-cyclohex-3-enyl)-methanol 
• 954148-52-8 C₁₇H₂₂O₃ 
• 954148-43-7 [(1R,6S)-1-(3-azido-propyl)-6-benzyloxymethyl-cyclohex-3-enylmethoxy]-triisopropyl-silane 
• 954148-42-6 3-((1R,6S)-6-benzyloxymethyl-1-(triisopropylsilanyloxy)methyl-cyclohex-3-enyl)-propan-1-ol 
• 954148-41-5 {(1R,6S)-6-benzyloxymethyl-1-[3-(4-methoxy-benzyloxy)-propyl]-cyclohex-3-enylmethoxy}-triisopropyl-silane 
• 954148-40-4 {(1R,6S)-6-(benzyloxymethyl)-1-[3-(4-methoxy-benzyloxy)-propyl]-cyclohex-3-enyl}-methanol 
• 954148-39-1 methyl (1R,6S)-6-(benzyloxymethyl)-1-(3-(4-methoxybenzyloxy)propyl)cyclohex-3-enecarboxylate 
• 954148-38-0 methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate 

Downstream Products

• 954148-46-0 N-[3-((1R,6S)-6-benzyloxymethyl-1-formyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide 
• 954148-47-1 (1R,2'S,6S,9a'S)-6-(benzyloxymethyl)-2'-(hydroxymethyl)-6',7',8',9a'-tetrahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-4'(3'H)-one 
• 954148-49-3 (1R,2'S,6S,9a'S)-6-(benzyloxymethyl)-2'-((triisopropylsilyloxy)methyl)-6',7',8',9a'-tetrahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-4'(3'H)-one 
• 954148-50-6 (1R,2S,2'S,6S,9a'S)-6-(benzyloxymethyl)-2-hydroxy-2'-((triisopropylsilyloxy)methyl)-6',7',8',9a'-tetrahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-4'(3'H)-one 
• 954148-51-7 (1R,2'S,6S,9a'S)-6-(benzyloxymethyl)-2'-((triisopropylsilyloxy)methyl)-6',7',8',9a'-tetrahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-2,4'(3'H)-dione 

Relevant academic research and scientific papers

The first synthesis of the ABC-ring system of 'upenamide

The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.