100762-43-4

Upstream product

• 100692-78-2 ethyl r-1,c-2,c-6,c-7-tetramethyl-4-oxobicyclo<4.3.0>non-3-yl acetate 
• 100692-71-5 r-1,c-5,c-6,c-9-tetramethylspirononane-3,2'-<1,3>dioxolan>-7-ol 
• 100692-75-9 r-1,c-5,c-6,c-9-tetramethylspirononane-3,2'-<1,3>dioxolan>-7-one 
• 76370-41-7 1-methoxy-4,5, anti-8-trimethylbicyclo<2.2.2>oct-5-en-2-one 
• 100692-67-9 (3aR,4S,7aS)-6-Methoxy-3a,4,7a-trimethyl-2,3,3a,4,5,7a-hexahydro-inden-1-one 
• 100692-70-4 r-1,c-5,c-6,9-tetramethylspironon-8-ene-3,2'-<1,3>dioxolan>-9-one 
• 100692-74-8 r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane>-7-one 
• 100692-69-1 r-1,c-5,c-6,9-trimethylspironon-7-ene-3,2'-<1,3>dioxolan>-9-one 
• 100692-68-0 r-1,c-5,c-6-trimethylspirononane-3,2'-<1,3>dioxolan>-9-one 
• 100692-73-7 r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane> 
• 100692-77-1 r-1,c-5,c-6,c-9-tetramethylbicyclo<4.3.0>nonan-3-one 
• 100692-79-3 r-4,c-4a,c-7,c-7a-tetramethyl-4,4a,5,6,7,7a,8,8a-octahydroindeno<5,6-b>furan-2-one 

Relevant academic research and scientific papers

Rearrangement Approaches to Cyclic Skeletons. IV. The Total Synthesis of (+/-)-Pinguisone and (+/-)-Deoxopinguisone Based on Photochemical Acyl Migration of a Bicyclonon-6-en-2-one

The total synthesis of (+/-)-Pinguisone (2) and (/-)-deoxopinguisone (3), fused ring sesquiterpenes, has been achieved starting from 1-methoxy-3,4,5-trimethylbenzene. 1-Methoxy-4,5,endo-8-trimethylbicyclonon-5-en-2-one (9) was prepared selectively via facial selective Diels-Alder reaction of the diene derived from the benzene and 2-chloroacrylonitrile.Ring enlargement of 9 using (CH3)3SiCHN2 and BF3 etherate gave the corresponding bicyclooct-en-2-one (8).The photochemical acyl migration of 8 gave the fused-ring compound (7).The fourth methyl was introduced selectively by the conjugate addition of (CH3)2CuLi to the spironon-8-ene-3,2'-dioxolan>-7-one prepared from 7.Each furan ring of 2 and 3 was constructed via the corresponding butenolide derived from the γ-keto acid by acid-catalyzed dehydration.

PHOTOCHEMICAL REARRANGEMENT APPROACH TO THE TOTAL SYNTHESIS OF (+/-)-PINGUISONE AND (+/-)-DEOXOPINGUISONE

The total synthesis of (+/-)-pinguisone and (+/-)-deoxypinguisone, the unusual fused-ring sesquiterpenes, was accomplished by the photochemical transformation of the bicyclonon-6-en-2-one into the bicyclonon-4-en-7-one.