DOI: 10.1055/a-2920-5526 ISSN: 0936-5214
Kornblum-Type Oxidative Ring-Opening Reaction of a Tricyclo[4.3.0.05,7]nonane Derivative for the Synthesis of a CD Ring System of Steroids
Hiroki Yamauchi, Hiroyuki Yamakoshi, Manato Uchida, Mai Ishikawa, Eisaku Ohashi, Seiichi NakamuraAbstract
We have developed a facile method for the transformation of a tricyclo[4.3.0.05,7]nonane derivative to a diastereomeric mixture of suitably oxygenated hydrindan isomers, wherein oxidative ring-opening, proton transfer, and deethoxycarbonylation sequentially proceeded in a single operation upon heating with Ni(OTf)2 in the presence of DABCO in DMSO at 150 °C.