130760-62-2

Upstream product

• 130760-83-7 C₁₉H₂₇NO₃S₂ 
• 130760-72-4 Acetic acid 2-[(1R,5S,6S)-5-(2-methanesulfonyloxy-ethyl)-6-methoxycarbonylamino-cyclohex-2-enyl]-ethyl ester 
• 149310-97-4 4-((1S,3aS,4R,5R,5aR,8aR,8bS)-4-Allyl-1-methyl-2-oxo-decahydro-furo[3,2-e]indol-5-yl)-butyric acid ethyl ester 
• 149310-96-3 (1S,3aS,4R,5R,5aR,8aR,8bS)-4-Allyl-1-methyl-2-oxo-5-(2-oxo-ethyl)-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester 
• 130760-79-1 (1S,3aS,4R,5R,5aR,8aR,8bS)-4-Allyl-5-(2-hydroxy-ethyl)-1-methyl-2-oxo-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester 
• 130760-76-8 (3aR,6R,7S,7aS)-7-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-2,3,3a,6,7,7a-hexahydro-indole-1-carboxylic acid methyl ester 
• 130760-78-0 (3aS,4R,5R,5aS,8aR,8bR)-4-Allyl-5-(2-hydroxy-ethyl)-2-oxo-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester 
• 130760-63-3 (3aR,4R,5S,5aS,8aR,8bR)-5-(2-Hydroxy-ethyl)-4-iodo-2-oxo-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester 
• 149310-98-5 C₁₇H₂₃NO₄ 
• 130760-82-6 C₁₈H₂₅NO₃ 
• 130760-71-3 Acetic acid 2-[(1S,5R,6R)-5-(2-hydroxy-ethyl)-6-methoxycarbonylamino-cyclohex-2-enyl]-ethyl ester 
• 130760-70-2 Acetic acid 2-((1S,5R,6R)-6-methoxycarbonylamino-5-vinyl-cyclohex-2-enyl)-ethyl ester 
• 130760-74-6 (3aR,5aR,8aS,8bS)-7-Oxo-2,3,3a,5a,7,8,8a,8b-octahydro-furo[2,3-g]indole-1-carboxylic acid methyl ester 
• 130760-73-5 (3aR,7S,7aR)-7-Carboxymethyl-2,3,3a,4,7,7a-hexahydro-indole-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of dl-Stenine

Intramolecular Diels-Alder cycloadduct 10 was converted to the Stemona alkaloid stenine (1) via a reaction sequence that features a Curtius rearrangement (12 -> 13), Eschenmoser-Claisen rearrangement (19 -> 20) and stereoselective free radical allylation

Studies on the synthesis of (±)-stenine: A combined intramolecular [4 + 2]-cycloaddition/rearrangement cascade

Several cyclic 2-(methylthio)-5-amidofurans containing tethered unsaturation were prepared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMSTF) with β-alkoxy-γ-dithiane lactams. Thermolysis of these furans resulted in an intramolecular Diels-Alder reaction (IMDAF). The resulting oxa-bridge cycloadducts underwent a subsequent 1,2-methylthio shift to form tricyclic lactams in high yield. Furan 9, annealed to an azepine ring, underwent the IMDAF reaction at or below room temperature. Conformational effects imposed by the placement of a carbonyl group within the tether, combined with a rotational bias about the C(2)-N bond, enhances the rate of the IMDAF reaction of the seven-ring system so that it occurs readily at 25 °C. The feasibility of using the cascade sequence in the context of a total synthesis of the Stemona alkaloid (±)-stenine was explored. The eventual synthesis of (±)-stenine was carried out by an intramolecular Diels-Alder reaction of a 2-amido-5-methylthio-substituted furan containing a trans-pent-3-enoic acid methyl ester side chain in order to create the desired azepinoindole skeleton. This was followed by a series of reductions to set the syn-anti stereochemical relationship at the incipient ring fusion sites present in stenine. All six stereocenters at the azepinoindole core were derived in high stereoselectivity from the functionality present in the rearranged cycloadduct 10. Compound 10 was converted to stenine in 11 additional steps via a sequence that features a Crabtree's-catalyst directed hydrogenation, iodolactonization, and a Keck allylation.

An expeditious total synthesis of (±)-stenine

(±)-Stenine was synthesized in eight steps from a known ketophosphonate reagent. The key step was an exo-selective Diels-Alder/intramolecular Schmidt domino reaction that afforded three of the four rings and four stereocenters in a single reaction. Copyright

Total synthesis of (+/-)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan.

[reaction: see text]. The intramolecular [4 + 2]-cycloaddition of a 2-methylthio-5-amidofuran was used to create the azepinoindole skeleton present in the Stemona alkaloid stenine. The rearranged cycloadduct was converted to stenine (1) in 11 additional steps via a sequence that features a Crabtree catalyst directed hydrogenation (9-->10), iodolactonization (2-->11), and a Keck allylation (11-->12).

Syntheses of the Stemona alkaloids (±)-stenine, (±)- neostenine, and (±)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction

A tandem Diels-Alder/azido-Schmidt reaction sequence provides rapid access to the core skeleton shared by several Stemona alkaloids including stenine, neostenine, tuberostemonine, and neotuberostemonine. The discovery and evolution of inter- and intramole