86558-55-6

Upstream product

• 41613-59-6 1-ethynyl-2,2,6-trimethyl-1-cyclohexanol 
• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 
• 86558-53-4 Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 20763-19-3 (methoxymethylene)triphenylphosphorane 

Downstream Products

• 123151-39-3 (4bR,10S)-2,10-Dimethoxy-4b,8,8-trimethyl-4b,5,6,7,8,10-hexahydro-phenanthrene-1,4-dione 
• 123151-35-9 2,10α-dimethoxy-4aβ,4b,5,6,7,8,10,10a-octahydro-4bβ,8,8-trimethyl-1,4-phenanthrenedione 
• 123151-36-0 3,10α-dimethoxy-4aβ,4b,5,6,7,8,10,10a-octahydro-4bβ,8,8-trimethyl-1,4-phenanthrenedione 
• 123749-05-3 1-Diazo-4-((S)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one 
• 374782-84-0 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one 
• 123749-06-4 3-((S)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid 
• 374782-77-1 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid 
• 123643-44-7 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1-buten-3-ol 
• 79563-01-2 (S)-1-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-ol 
• 123643-43-6 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionaldehyde 
• 123643-43-6 3-((S)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionaldehyde 
• 123643-45-8 ethyl 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-2-butenoate 
• 123643-47-0 [(2R,3R)-3-(2,6,6-Trimethyl-cyclohex-1-enylmethyl)-oxiranyl]-methanol 
• 123643-48-1 (2S,3R)-2-Iodomethyl-3-(2,6,6-trimethyl-cyclohex-1-enylmethyl)-oxirane 

Relevant academic research and scientific papers

Enantiocontrolled synthesis of quaternary carbon centers via anionic oxy-cope rearrengement: An efficient synthesis of (+)-dihydromayurone

(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed vai chairlike transition state with the equatorial oxyanionic bond.

A New General Synthetic Approach to Diterpenes: Application to Syntheses of (+ -)-Taxodione and (+ -)-Royleanone.

High-pressure Diels - Alder reactions of 1,3,3-trimethyl-2-vinyl-1-cyclohexenes 3a,b,i with substituted 1,4-benzoquinones afford, in good yield, highly functionalized tricyclic ring systems which are found in many classes of naturally occuring terpenes.Notably, the reactions of 3a are highly regio- and stereoselective.Efficient, formal syntheses of antitumor diterpenes (+ -)-taxodione and (+ -)-royleanone are reported, which demonstrate the practical application of this new strategy for the preparation of varied terpene systems.Of particular interest is that the high-pressure reactions are accelerated by mild Lewis acids and the regio- and stereoselectivity of these reactions is also improved under the combined high-pressure / Lewis acid conditions in comparison to the high-pressure conditions alone.Indeed, in the reaction of 3a with 2-methoxy-5-methyl-1,4-benzoquinone, ZnBr2 is required to effect the Diels-Alder reaction even at 12 kbar, and endo adduct 12c is formed stereoselectively in 90percent yield.In contrast, low-temperature Ti(IV)-catalyzed reactions of diene 3a with methoxy-substituted 1,4-benzoquinones at atmospheric pressure regioselectively produce dihydrobenzofurans 19 and 20, apparently via alkylation of the quinone Ti(IV) complex by the diene followed by the ring closure.

SYNTHESE TOTALE DU (+/-)POLIGODIAL, DE LA DRIMENINE ET DE COMPOSES APPARENTES A JONCTION DE CYCLE cis ET trans

Isomerization by base under kinetic or thermodynamic control of the Diels-Alder adduct of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with dimethyl acetylene dicarboxylate leads to two isomers which, after catalytic hydrogenation, give in high yield starting materials for synthesis of trans and cis drimanes.A short total synthesis of (+/-)-polygodial and (+/-)-drimenine from one of these isomers is desribed.