29073-38-9

Upstream product

• 94023-80-0 Acetic acid (3aR,5R,6R,7R,7aS)-5-acetoxy-7-(6-acetoxymethyl-benzo[1,3]dioxol-5-yl)-1-methyl-2-oxo-octahydro-indol-6-yl ester 
• 94013-29-3 Acetic acid 6-((1aR,2aS,5aR,6S,6aS)-5-methyl-4-oxo-octahydro-1-oxa-5-aza-cyclopropa[f]inden-6-yl)-benzo[1,3]dioxol-5-ylmethyl ester 
• 94013-31-7 Acetic acid 6-((3aR,7R,7aS)-1-methyl-2-oxo-2,3,3a,4,7,7a-hexahydro-1H-indol-7-yl)-benzo[1,3]dioxol-5-ylmethyl ester 
• 94013-30-6 (3aS,7S,7aR)-7-Benzo[1,3]dioxol-5-yl-1-methyl-1,3,3a,4,7,7a-hexahydro-indol-2-one 
• 94013-32-8 (3aR,7R,7aS)-7-Benzo[1,3]dioxol-5-yl-1,3,3a,4,7,7a-hexahydro-indol-2-one 
• 42390-68-1 methyl 2c-(N-methoxycarbonylamino)-3t-(3,4-methylenedioxyphenyl)cyclohex-4-enyl-r-acetate 
• 94013-22-6 C₁₇H₁₇NO₆ 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Total synthesis of the Amaryllidaceae alkaloid clivonine

Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler-Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (-)-20 and (±)-28 are also reported.

Total synthesis of (±)-8-Oxo-erythrinine, (±)-8-oxo-erythraline, and (±)-clivonine

Total syntheses of the erythrina alkaloids (±)-8-oxo-erythrinine and (±)-8-oxo-erythraline have been developed, based on a substrate-controlled intramolecular 6-exo-trig selective radical spirocyclization that establishes the quaternary center of the B-ri

Total synthesis of the lycorenine-type amaryllidaceae alkaloid (±)-Clivonine via a biomimetic ring-switch from a lycorine-type progenitor

A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.

SYNTHESIS OF AN AMARYLLIDACEAE ALKALOID, (+/-)-HIPPEASTRINE

Total synthesis of one of Amaryllidaceae alkaloids, hippeastrine, was accomplished starting from methyl 2c-(N-methoxycarbonylamino)-3t-(3,4-methylenedioxyphenyl)cyclohex-4-enyl-r-acetate in stereoselective manner.