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An 8π Electron Electrocyclization Leading to a 9,19-Methano-Bridged Analogue of 1α,25-Dihydroxyvitamin D3

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journal contribution
posted on 13.02.2002, 00:00 by Rena Hayashi, Susana Fernández, William H. Okamura
Lindlar semihydrogenation of a vitamin D type trienyne leads spontaneously to 9α,19-methano-1α,25-dihydroxyvitamin D3. The intermediate tetraene resulting from the reduction undergoes a rapid, stereoselective 8π electron electrocyclization affording a novel steroid containing a linearly fused ABC (six-eight-six) 1,3,5-cyclooctatriene carbon framework.