176979-95-6

Upstream product

• 176979-92-3 Methanesulfonic acid (6R,8S)-8-methanesulfonyloxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-ylmethyl ester 
• 176980-00-0 (6R,8S)-1-(2,2-Dimethyl-propionyl)-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole-6,8-dicarbaldehyde 
• 176979-91-2 ((6R,8S)-8-Hydroxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-yl)-methanol 
• 75-36-5 acetyl chloride 
• 176979-93-4 (6R,8S)-6,8-Dimethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole 

Downstream Products

• 107368-93-4 (6R,8S)-cis-trikentrin B 

Relevant academic research and scientific papers

Enantioselective total synthesis of cis-trikentrin B

Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.