327162-12-9

Upstream product

• 77-78-1 dimethyl sulfate 
• 327162-11-8 4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one 
• 178241-50-4 methyl (1S,2R,4aR,8S,8aR)-1,2,3,4a,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalen-4(5H)-one-1-carboxylate 
• 178241-41-3 O-[(1S,2R,4aR,8S,8aR)-methyl-1,2,3,4a,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalen-4(5H)-one-1-carboxylate-8-yl]thiocarboxyimidazolide 
• 327162-08-3 methyl 5-hydroxy-5-[(1R,2R,4aR,8S,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthyl]-3-oxopentanoate 
• 327162-07-2 (1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthalene-1-carbaldehyde 
• 327162-00-5 methyl (1S,2R,4aR,8S,8aR)-1,2,3,4a,6,7,8,8a-octahydro-8-(tert-butyldimethylsilyloxy)-2-methylnaphthalen-4(5H)-one-1-carboxylate 
• 327162-09-4 methyl 5-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3,5-dioxopentanoate 
• 327161-99-9 3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene 
• 327162-04-9 O-[methyl (1R,2R,4S,4aR,8aR)-decahydro-2-methylnaphthalene-1-carboxylate-4-yl] S-methyl dithiocarbonate 
• 327162-10-7 4-hydroxy-6-[(1R,2R,4aR,8S,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthyl]-2H-pyran-2-one 
• 327162-02-7 methyl (1S,2R,4S,4aR,8aR)-decahydro-4-hydroxy-2-methylnaphthalene-1-carboxylate 
• 327162-03-8 methyl (1R,2R,4S,4aR,8aR)-decahydro-4-hydroxy-2-methylnaphthalene-1-carboxylate 
• 327162-01-6 methyl (1S,2R,4aR,8aR)-1,2,3,4a,6,7,8,8a-octahydro-2-methylnaphthalen-4(5H)-one-1-carboxylate 

Downstream Products

• 327162-13-0 4-methoxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylsulfinylmethyl-2H-pyran-2-one 

Relevant academic research and scientific papers

First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol

The phytotoxins solanapyrones D (1) and E (2) have been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. The decalone was transformed into a solanapyrone core by equilibration into thermodynamically stable trans-decalone (11), dehydroxylation, and dehydration. Condensation of a methyl acetoacetate equivalent followed by cyclization installed a pyrone moiety. Introduction of a formyl or hydroxymethyl unit into the pyrone ring via Pummerer related reactions furnished solanapyrones D (1) and E (2).

The first total synthesis of (-)-solanapyrone E based on domino Michael strategy.

[figure: see text] A phytotoxin, solanapyrone E, has been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. After several transformations on the decalone