139751-01-2

Upstream product

• 154634-82-9 (1R,2S,5S,6R,7S)-(+)-5-methoxy-4-<4'-(phenylthio)but-3'-ynyl>-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 139750-99-5 (1R,2S,6R,7S)-4-But-3-ynyl-5-methoxy-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 139750-90-6 (1R,2S,5R/S,6R,7S)-(+)-4-(but-3'-ynyl)-5-hydroxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 64-18-6 formic acid 
• 139751-00-1 (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 154634-81-8 (1R,2S,5S,6R,7S)-(+)-4-(but-3'-ynyl)-5-methoxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 

Downstream Products

• 3348-73-0 (+)-laburnine 

Relevant academic research and scientific papers

Enantioselective Synthesis of (+)-Indolizidine, (+)-Laburnine and (+)-Elaeokanines A and C using the Diels-Alder Reaction of α-(2-eyo-Hydroxy-10-bornylsulfinyl)maleimide

The Diels-Alder adduct 5 derived from the N-butynylmaleimide 6 and cyclopentadiene has been transformed into the tetracyclic lactams 12 and 19 via a common precursor 9.The lactams 12 and 19 have been converted into (+)-indolizidine 1 and (+)-laburnine 2, respectively, via retro-Diels-Alder reaction.Similar methodology has bee succesfully applied to the synthesis of (+)-elaeokanine A 3 and (+)-elaeokanine C 4.

A Novel Approach to Bicyclic Alkaloids Using a Tandem Diastereoselective Acyliminocyclization and Retro Diels-Alder Reaction Sequence. Synthesis of (+)-Indolizidine and (+)-Laburnine

A new aproach to diastereoselective cationic cyclization by stereocontrol due to the bicycloheptene moiety in a chiral γ-hydroxy lactam is described.The diastereoselective reaction followed by Diels-Alder cycloreversion has ben succesfully applied to a chiral synthesis of (+)-indolizidine and (+)-laburnine (=trachelanthamidine).