Hydrindane framework

A multi-step asymmetric synthesis of a hydrindane framework was achieved in water via asymmetric allylic alkylation, propargylation and aquacatalytic cycloisomerization of a 1,6-enyne, where all three steps were performed in water with the recyclable polymeric catalysts. The racemic cyclohexenyl ester 27 reacted with diethyl malonate under the conditions mentioned in Table 6.1 to give 90-92% ee of 34b. The polymeric chiral palladium complex 23-Pd was reused four times... 

Scheme 6,5 Asymmetric multistep synthesis of a hydrindane framework in water.

Akiyama s group developed an anodic oxidative decarboxylation of oxabi-cyclo [2.2.1] substrates that subsequently undergo skeletal rearrangement to yield 1,2,3-trisubstituted cyclopentanols [146, 147]. An example of this reaction which generates the carbocyclic framework of hydrindanes is shown in Eq. 99. 

In continuation of our interest in designing new methodology based on the chemistry of cyclohexa-dienone and photoreaction of P,Y-enones, " 2 developed a new stereoselective route to sterpuranes, another class of sesquiterpenes containing a tricyclic framework wherein the cyclobutane ring is fused with a hydrindane unit in a linear fashion. In this context, the tricycHc P,y-enones of type 235 were synthesized and their photochemistry was examined upon direct as weU as sensitized irradiation. The desired tricycHc compound 235, containing a P,y-enone chromophore, was prepared from hydroxyme-thylphenol 232. Oxidation of 232 with sodium metaperiodate generated the cyclohexadienone 233, which... 

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