215609-79-3

Upstream product

• 108-24-7 acetic anhydride 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 215609-92-0 2-(3,4-methylenedioxyphenyl)-3-[(diethylphosphoryl)oxy]-1-cyclohexene 
• 215609-74-8 2-(3,4-methylenedioxyphenyl)-3-[(methoxycarbonyl)oxy]-1-cyclohexene 
• 40597-44-2 N-(2,2-diethoxy-ethyl)-4-methylbenzenesulfonamide 
• 215609-78-2 (S)-2-(3,4-methylenedioxyphenyl)-3-[(N-p-tolylsulfonyl)-2,2-diethoxyethylamino]-1-cyclohexene 
• 215609-75-9 N-((S)-2-Benzo[1,3]dioxol-5-yl-cyclohex-2-enyl)-4-methyl-N-(2-oxo-ethyl)-benzenesulfonamide 
• 215609-76-0 (3R,3aS,7aS)-N-p-tolylsulfonyl-3-hydroxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole 

Downstream Products

• 677301-66-5 (3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole 
• 215609-85-1 (3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole 
• 215609-83-9 (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole 
• 677301-64-3 (3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-formyloxy-2,3,3a,6,7,7a-hexahydroindole 
• 23610-70-0 (+)-11-hydroxyvattitine 
• 17245-16-8 pretazettine 
• 639-41-8 (+)-crinamine 
• 215609-81-7 (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole 

Relevant academic research and scientific papers

Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids

The thermally induced electrocyclic ring-opening of C2-symmetric (meso) 6,6-dibromobicyclo[3.1.0]hexanes such as 10 in the presence of the chiral, nonracemic 1°-amine 28 afforded a ca. 1:1 mixture of the diastereoisomeric and chromatographically separable 1-amino-2-bromo-2-cyclohexenes 37 (42%) and 38 (45%). Each of these was elaborated over 13 steps, including Suzuki-Miyaura cross-coupling, radical cyclization, and Pictet-Spengler reactions, into (-)- or (+)-crinane (1 or ent-1, respectively). Variations on these protocols were applied to the total syntheses of (+)- and (-)-11-hydroxyvattitine [(+)- and (-)-3], (+)- and (-)-bulbispermine [(+)- and (-)-4], (+)- and (-)-haemanthamine [(+)- and (-)-5], (+)- and (-)-pretazettine [(+)- and (-)-6], and (+)- and (-)-tazettine [(+)- and (-)-7] as well as (±)-hamayne [(±)-8] and (±)-apohaemanthamine [(±)-9]. A number of these alkaloids were synthesized for the first time.

Palladium-Catalyzed Asymmetric Allylic Substitution of 2-Arylcyclohexenol Derivatives: Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

Much interest has been shown in Amaryllidaceae alkaloids as synthetic targets due to their wide range of biological activities. Over 100 alkaloids have been isolated from members of the Amaryllidaceae family; most of them can be classified into eight skel