79 4,4-Dimethyl-1α,2α-epoxycholestane骨格のA/B環の5/7員環への変換
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6β-Bromo-4,4-dimethyl-1α,2α-epoxy-3α,5α-oxidocholestane (1) was obtained from 4 by bromination with NBS. On acidic treatment, the bromo-epoxy-oxide (1) was transformed into 5β-bromo-4,4-dimethyl-3α,6α-oxido-5(10→1βH)abeo-10(19)-cholesten-2α-ol (2a), which gave a diol (11) on reduction. On oxidation with lead tetraacetate, the diol (11) gave a dialdehyde (13). When the diol (11) was oxidized with m-chloroperbenzoic acid and successive acetylation, acetoxyl alcohols (9b) and (14) were obtained. On the basis of the similarity of both NMR spectra of 9a and 9b, the structure of 2a was determined.
- 天然有機化合物討論会の論文
- 1978-08-22
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- 79 4,4-Dimethyl-1α,2α-epoxycholestane骨格のA/B環の5/7員環への変換