Total Synthesis of (.+-.)-β-Microbiotene (I), (.+-.)-Microbiotol (II), (.+-.)-Cyclocuparanol (III) and (.+-.)-β-Cuparenones (IV).

Srikrishna, A. ; Ramachary, D. B. (2007) Total Synthesis of (.+-.)-β-Microbiotene (I), (.+-.)-Microbiotol (II), (.+-.)-Cyclocuparanol (III) and (.+-.)-β-Cuparenones (IV). ChemInform, 38 (38). ISSN 0931-7597

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Official URL: http://doi.org/10.1002/chin.200738174

Related URL: http://dx.doi.org/10.1002/chin.200738174

Abstract

Total synthesis of (+/-)-beta-microbiotene, (+/-)-microbiotol, (+/-)-cyclocuparanol and their epirners along with (+/-)-beta-cuparenone has been described. A combination of orthoester Claisen rearrangement, an acid catalysed rearrangement of a diazoketone for the generation of bicyclo[4.2.1]nonanedione, a retro-Claisen condensation and an intramolecular diazoketone cyclopropanation reaction have been employed for the construction of three contiguous quaternary atoms present in cyclocuparanes.

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