218628-44-5

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 60178-25-8 ethyl α-chloro-α-(phenylthio)acetate 
• 7605-25-6 ethyl phenylsulfenylacetate 

Downstream Products

• 250261-59-7 N-(Cyclohex-2-enyl)-N-(4-methoxybenzyl)-2-(3,4-methylenedioxyphenyl)-2-(phenylthio)acetamide 
• 218628-45-6 2-(3,4-Methylenedioxyphenyl)-2-(phenylthio)acetic acid 
• 951327-62-1 C₂₃H₂₅NO₅ 
• 951327-61-0 C₂₇H₃₃NO₇ 
• 951327-60-9 C₂₇H₃₁NO₈ 
• 951327-58-5 C₃₃H₃₆ClNO₈S 
• 951327-57-4 C₃₃H₃₆BrNO₈S 

Relevant academic research and scientific papers

Chemoenzymatic approaches to the montanine alkaloids: A total synthesis of (+)-brunsvigine

The readily available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1].

Stereoselective synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol2-ones using radical cyclisation: A formal synthesis of (±)-pancracine

The Bu3SnH- or (TMS)3SiH-mediated 5-emlo-trig radical cyclisation of the 7V-(cyclohex-l-enyl)acetamide 10 gives a mixture of the as-fused (3R*,3aS*,7aS*)- and trans-fused (3R*,3aS*,7aK*)-3-aryloctahydroindol-2-ones lia and lib, whereas the 5-cxo-trig radical cyclisation of the N-(cycIohex-2-enyl)acetamide 17 proceeds in a stereoselective manner to give only lia. The latter method has been applied to the synthesis of the 5,11-methanomorphanthridine derivative 30, a key intermediate for the synthesis of (±)-pancracine 1.

Formal synthesis of (±)-pancracine using stereoselective radical cyclization of N-(2-cyclohexenyl)-α-aryl-α-(phenylthio)acetamide

(Me3Si)3SiH-mediated 5-exo-trig radical cyclization of N-(2-cyclohexcnyl)-α-aryl-α-(phenylthio)acetamide 19 proceeded in a stereoselective manner to give (3R*,3aS*,7aS*)-3-aryloctahydroindol-2-one 20. The product was transformed into the key intermediate 25 for the synthesis of (±)-pancracine (1), a montanine-type Amaryllidaceae alkaloid.