27150-29-4

Upstream product

• 50-00-0 formaldehyd 
• 6846-34-0 (1S,4S,7S,8R,11R,12R,13S)-13-isopropyl-12-methyl-10-oxa-2-azatetracyclo<5.4.1.1.^8,11.0^4,12>tridecan-9-one 
• 36326-38-2 ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate 
• 40142-17-4 rac-dendrobane-2,12-dione 
• 53375-97-6 methyl N-methyl-11α-methyl-7-keto-6α-(2-propyl)-2,3,4,5,6,8α,9α,10α-octahydrocyclopentenoindole-5β-carboxylate 
• 67496-16-6 methyl 1β-hydroxymethyl-7aα-methyl-5α-(2-propyl)-2,3,3aα,4,5,7a-hexahydro-1H-indene-4β-carboxylate 
• 187986-27-2 (1R,2S,6R,8R,10R,11S)-11-isopropyl-10-methoxy-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one 
• 345665-15-8 Acetic acid (2aS,6R,7R,7aS,7bR)-6-isopropyl-1,7b-dimethyl-4-oxo-4a-phenylselanyl-decahydro-cyclopenta[cd]indol-7-yl ester 
• 242130-43-4 Acetic acid (2aS,4aS,5R,6S,7R,7aS,7bS)-5-cyano-6-isopropyl-1,7b-dimethyl-4-phenoxythiocarbonyloxy-decahydro-cyclopenta[cd]indol-7-yl ester 
• 242130-32-1 (+)-(1S,4S,5R,6S,7R,8S,11R)-5-acetoxy-7-cyano-6-isopropyl-3,11-dimethyl-3-azatricyclo-[6.2.1.0^4,11]undecan-9-one 
• 242130-34-3 (+)-(1S,4S,5R,6S,7R,8S,11R)-5-acetoxy-7-cyano-6-isopropyl-3,11-dimethyl-3-azatricyclo-[6.2.1.0^4,11]undecane 
• 242130-29-6 (+)-(1S,4S,5R,6R,8S,11R)-5-acetoxy-6-isopropyl-3,11-dimethyl-3-azatricyclo-[6.2.1.0^4,11]undecan-9-one 
• 242130-31-0 acetic acid 6-isopropyl-1,7b-dimethyl-4-oxo-2,4,4a,5,6,7,7a,7b-octahydro-1H-1-aza-cyclopenta[cd]inden-7-yl ester 
• 242130-30-9 (+)-(1S,4S,5R,6S,11R)-5-acetoxy-6-isopropyl-3,11-dimethyl-3-azatricyclo-[6.2.1.0^4,11]undec-7-en-9-one 

Relevant academic research and scientific papers

Catalytic Enantioselective Total Synthesis of the Picrotoxane Alkaloids (-)-Dendrobine, (-)-Mubironine B, and (-)-Dendroxine

A concise enantioselective total synthesis of three sesquiterpenoid alkaloids - (-)-dendrobine, (-)-mubironine B, and (-)-dendroxine - is presented, which highlights the state-of-art catalytic methods, including enantioselective Diels-Alder cycloaddition, iron-catalyzed aerobic lactonization, copper-catalyzed cycloisomerization, and free-radical-initiated hydroazidation.

Total synthesis of (-)-dendrobine

Cascading to alkaloids: An 18-step total synthesis of (-)-dendrobine is based on a reaction cascade with a key amine group (see scheme, Bn=benzyl). The amine is the initiator of the cascade and provides an efficient method for installing the stereocenters at C11 and C3. The overall transformation occurs stereoselectively only when the conversion is carried out without the isolation of intermediates. Copyright

A short synthesis of (-)-dendrobine. Some observations on the nickel mediated radical cyclisation and on the Pauson-Khand reaction

The total synthesis of (-)-dendrobine was accomplished in 13 steps starting from (+)-verbenol. The key step is a radical cascade starting with a carbamyl radical generated by reaction of the N-benzoyloxy-carbamyl derivative of trans-verbenol with tributyl

Total synthesis of (-)-dendrobine via α-carbonyl radical cyclization

An efficient total synthesis of enantiomerically pure (-)-dendrobine (1) is accomplished based on an α-carbonyl radical cyclization reaction. (S)- carvotanacetone (6) was convened to bicyclic acetal-enone 4 in five steps. Cul-mediated conjugate addition o

Acylnitrilium ion initiated heteroannulations in alkaloid synthesis. An efficient, stereocontrolled, total synthesis of the Orchidaceae alkaloid (±)-dendrobine

A concise total synthesis of (±)-dendrobine is described that proceeds in eight steps from 2-methylcyclopent-2-en-1-one. The key transformation in this approach is the silver ion mediated cyclocondensation of the isonitrile 6 with the acyl chloride 5. Thi

Total Synthesis of (+/-)-Dendrobine

A total synthesis of (+/-)-dendrobine is described. (E,E,E)-Triene 9a, available stereoselectively in six steps from methyl 4-(diethylphosphono)crotonate, cyclizes by an intramolecular Diels-Alder reaction to afford 75-83percent of a mixture of four perhydroindanols containing 83percent of endo isomers 8a and 8b.Epimers 8a and 8b were transformed into nitrile 25 by two separate routes, each of which involves epimerization of C4, oxidation, angular methylation, and reductive cyanation.Nitrile 25 served as a precursor of amino ester 3 by two separate routes, the most efficient of which proceeded via bromolactone 40.Epoxidation of the trichloroethylurethane 58 prepared from 3 afforded a mixture of two epoxides, both of which were utilized in the synthesis.The minor epoxide, 59 (38-40percent yields), was transformed into dendrobine via methyl ketodendrobinate 57, while the major epoxide 60 (45-48percent yields) was recycled to 58.Additional strategies for the synthesis of dendrobine from 3 are discussed.