Lilac alcohol synthesis

Treatment of the selenide (19) with unbuffered 30% hydrogen peroxide-THF yields the cis- and trans-linalyl oxides (247) via [2,3] sigmatropic rearrangement. Kossanyi et al. have improved upon the efficiency of Vig s synthesis of the four lilac alcohols (248). The synthesis of the furanoid (249), formed during sulphuric acid-catalysed dimerization of isoprene, is straightforward. The known half-... 

The cycloadduct (75d) has been utilized for the synthesis of nonactic acid (116) and lilac alcohol (119) via (118). The Prelog-Djerassi lactone (117), a pivotal intermediate in Masamune s methymycin synthesis, has been prepared tom the key compound (75e) (Scheme 21)J ... 

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