72496-32-3

Upstream product

• 118197-99-2 (3R*,3aS*)-methyl 2,3,3a,6,7,7a-hexahydro-7-hydroxy-3,3a-dimethyl-1,5(4H)-dioxoindene-7a-carboxylate 
• 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 
• 100692-73-7 r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane> 
• 100692-67-9 (3aR,4S,7aS)-6-Methoxy-3a,4,7a-trimethyl-2,3,3a,4,5,7a-hexahydro-inden-1-one 
• 100-39-0 benzyl bromide 
• 100692-71-5 r-1,c-5,c-6,c-9-tetramethylspirononane-3,2'-<1,3>dioxolan>-7-ol 
• 6076-81-9 dimethyl meso-3,4-dimethylhexane-1,6-dioate 
• 15474-81-4 (3R^*,4S^*)-3,4-dimethylhexanedioic acid 
• 72446-23-2 (4R*,4aS*,7R*,7aS*)-4,4a,6,7a,8-hexahydro-4,4a,7,7a-tetramethylindeno<5,6-b>furan-3(2H),5-dione 
• 15681-48-8 lithium dimethylcuprate 
• 79866-14-1 6,7-didehydro-7-norpinguisone 
• 100692-74-8 r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane>-7-one 
• 100692-68-0 r-1,c-5,c-6-trimethylspirononane-3,2'-<1,3>dioxolan>-9-one 

Relevant academic research and scientific papers

Total Synthesis of Pinguisone

A stereoselective total synthesis of pinguisone (1) from known (S)-(+)-2,3,7,7a-tetrahydro-7a-methyl-6H-indene-1,5-dione (3) is described.The utilization of common intermediates in the synthesis of pinguisone-like and 7-epi-pinguisone-like compounds is discussed.

Synthetic Studies towards the Pinguisanes; Synthesis of 4-epi-Pinguisone

Two procedures have been developed for the synthesis of the appropriate indene skeleton required for construction of pinguisone and 4-epi-pinguisone.Whereas 1-methoxy-3-(trimethylsiloxy)buta-1,3-diene (Danishefsky's diene) was completely unreactive toward

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.