22489-40-3

Usage

InChI:InChI=1/C15H20O2/c1-9-7-13(16)15(4)10(2)11-5-6-17-12(11)8-14(9,15)3/h5-6,9-10H,7-8H2,1-4H3/t9-,10-,14+,15-/m1/s1

Upstream product

• 15681-48-8 lithium dimethylcuprate 
• 79866-14-1 6,7-didehydro-7-norpinguisone 
• 121944-81-8 1β,8β,9β,12β-tetramethyl-3αH-5-oxo-4-oxatricyclo<7.3.0.0^3,7>dodec-6-en-10-one 
• 79866-13-0 7-isopropylthio-7-norpinguisone 
• 79866-12-9 2,3-dihydro-7-isopropylthio-3-oxo-7-norpinguisone 
• 79898-06-9 (+)-(3aR,7aS)-3a,7a-dihydro-3a,7a-dimethyl-4H-indene-1,5-dione 
• 79872-76-7 (+)-(3S,3aR,7aS)-2,3,3a,7a-tetrahydro-3-isopropylthio-3a,7a-dimethyl-4H-indene-1,5-dione 
• 55339-75-8 2,6-dimethyl-2-propenylcyclohexanone 
• 773-24-0 2-hydroxy-1,5-dimethylbicyclo <3.3.1> nonan-9-one 
• 121944-72-7 1,5-dimethylbicyclo <3.3.1> nonan-2,9-dione 
• 121944-67-0 2-(3-bromopropyl)-2,6-dimethylcyclohexanone 
• 121944-69-2 2-(3-hydroxypropyl)-2,6-dimethylcyclohexanone 
• 121944-63-6 3β,3aβ,7,7aβ-tetramethyl-2,3,3a,4,5,7a-hexahydroinden-1-one 
• 121944-70-5 3-(2-oxo-1,3-dimethylcyclohexyl)-propanale 

Relevant academic research and scientific papers

BICYCLO NONANE APPROACH TO PINGUISANE TERPENOIDS.TOTAL SYNTHESIS OF (+/-) PINGUISONE

The total synthesis of (+/-) pinguisone 1, the sterically crowded unusual fused-ring sesquiterpene, was accomplished by synthetic elaboration of the 3β,3aβ,7,7aβ-tetramethylbicyclo non-6-en-1-one 2a prepared by acid catalyzed rearrangement o

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.

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.