119439-13-3

Upstream product

• 119439-12-2 C₁₉H₂₆O₂S 
• 119439-10-0 (2R,3aS,7aS)-4-Methoxy-3a,7a-dimethyl-1-methylene-octahydro-inden-2-ol 
• 931-59-9 benzenesulfenyl chloride 
• 119439-10-0 (2S,3aS,7aS)-4-Methoxy-3a,7a-dimethyl-1-methylene-octahydro-inden-2-ol 
• 60975-75-9 (3aS,7aR)-4-Methoxy-3a,7a-dimethyl-octahydro-inden-1-one 
• 86000-40-0 trans-1,6-dimethyl-7-methylene-2-methoxybicyclo<4.3.0>nonane 
• 119439-11-1 (3aS,7aR)-4-Methoxy-3a,7a-dimethyl-1-methylene-octahydro-inden-2-one 

Downstream Products

• 119459-33-5 (3aS,7aR)-3-[(S)-1-((S)-Benzenesulfinyl)-ethyl]-7-methoxy-3a,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-1H-indene 

Relevant academic research and scientific papers

A MODEL FOR TRITERPENE SIDE-CHAIN SYNTHESIS. 2

A bicyclic model for 17-keto derivatives of triterpenes, trans-1,6-dimethyl-2-methoxybicyclononan-7-one, was used to explore side-chain construction concurrent with oxidation at C-8 (triterpene C-16).Oxidation of methylene derivative 2 with selenium dioxide gave β alcohol 14, and borohydride reduction of the corresponding ketone (15) led to the α epimer 16.Each allylic alcohol (14 and 16) reacted stereospecifically with phenylsulfenyl chloride to give, respectively, diastereoisomeric sulfoxides 20 and 19.The latter yielded a conjugate base that was methylated selectively to give sulfoxide 21.Desulfuration of 21 with trimethylphosphite generated the ethylidene α alcohol 22, and following PDC oxidation, E enone 25.This enone was a minor product from an alternative synthesis beginning with ethylidene derivative 3.Treatment of 3 with selenium dioxide followed by PDC gave the isomeric Z enone 24 as the major product.Reaction of 24 with lithium bis-4-methyl-3-pentenylcuprate proceeded by a facial-selective conjugate addition to the euphane CD model 26.The E isomer 25, under similar conditions, gave only an unresolved mixture.These results are compared with similar steroid reactions reported by Trost and Schmuff.