138253-17-5

Upstream product

• 62708-47-8 Dimethyl 3,7-dioxobicyclo<3.3.0>octane-2,6-dicarboxylate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 138253-18-6 2,6-Dibenzyl 2,6-bis<(3,4-methylenedioxy)phenyl>-3,7-dioxobicyclo<3.3.0>octane-2,6-dicarboxylate 

Relevant academic research and scientific papers

A new stereo- and regioselective synthesis of (±)-sesamin involving a β-scission of alkoxyl radicals as the key step1

A new stereo- and regioselective synthesis of (±)-sesamin (a representative lignan) based on our general method for the transformation of a cyclopentanone ring into a tetrahydrofuran ring involving a regioselective β-scission of the alkoxyl radicals is reported.

Photoinduced molecular transformations. 157. A new stereo- and regioselective synthesis of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans involving a β-scission of alkoxyl radicals as the key step. New total syntheses of (±)-sesamin, (±)-eudesmin, and (±)-yangambin

New total syntheses of naturally occurring 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans, (±)-sesamin and (±)-eudesmin, and the first total synthesis of (±)-yangambin were achieved according to a general method devised by Suginome and colleagues for replacing the carbonyl group of the cyclopentanone ring with an oxygen atom to give a corresponding tetrahydrofuran ring involving a regioselective β-scission of alkoxyl radicals; arylation of dimethyl, diallyl, or dibenzyl 3,7-dioxobicyclo[3.3.0]octane-2,6-dicarbonate (18 and 19a,b) with aryllead triacetate 9a-c, followed by dealkoxycarbonylation of the resulting arylated product 20a-f, gave 2,6-diaryl-3,7-dioxobicyclo[3.3.0]octane 21a-c. A regioselective Baeyer-Villiger oxidation of 21a-c with m-CPBA-NaHCO3 or -K2CO3 gave the corresponding δ-lactone 22a-c, which was reduced with DIBAL to give the corresponding lactol 23a-c. The irradiation of a solution of the hypoiodite of 23a-c, generated in situ with mercury(II) oxide-iodine, in benzene with Pyrex-filtered light resulted in a regioselective β-scission of the corresponding alkoxyl radical to give iodo formate 24a-c. Heating 24a-c in MeOH with NaBH4 gave (±)-sesamin (25a), (±)-eudesmin (25b), or (±)-yangambin (25c).