Stereoselective Synthesis of Dimethyl TETRACYCLO[5.2.1.02.6.03.8]DECANE-7,8-DICARBOXYLATE

Abstract

A short synthesis of the titled compound, a possible intermediate to prepare dodecahedrane, whose key-steps are the stereoselective trimethylene-annelation in the C2 and C3 positions of dimethyl 7,7-diethoxynorbornane-2,3-dicarboxylate and the high-yield intramolecular C–H insertion of a carbene generated from a 10-oxotricyclo[5.2.1.02.6]decane derivative, is described.

Double Methylenecyclopentane Annulation of Succinimides: Easy Access to 3,7‐Dioxobicyclo[3.3.0]octane‐1,5‐dicarboximides

“…[10] Moreover, we had experience in the formation of cyclopentane derivatives by alkylation of a dianion derived from an N-aryl-α,αЈ-disubstituted succinimide with 1,3-dibromopropane using LDA as the base, [11] following a known procedure. [12] Consequently, we imagined that reaction of N-substituted succinimides 4 with an excess of a base, such as LDA, and an excess of the alkylating agent 5 might give imides 6 which could be further alkylated to give finally imides 7 (Scheme 1).…”