Elsevier

Bioorganic Chemistry

Volume 7, Issue 2, June 1978, Pages 215-220
Bioorganic Chemistry

A new method for selective epoxidation and a biogenetic-type synthesis of linalyloxides

Dedicated to Professor William S. Johnson on the occasion of his 65th birthday.
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Abstract

[2.3]Sigmatropic rearrangement and successive selective epoxidation of geranyl selenide (2), citronellyl selenide (4), and farnesyl selenide (6) are described, and a simple synthesis of trans-(15) and cis-linalyloxides (16) along biosynthetic lines is also reported.

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    Citation Excerpt :

    Altering the nature of the leaving group offered no advantages (Scheme 3 and Table 2).8 Methyl carbonate 59 gave very similar results to acetate 3a, while tertiary acetate 6, derived from (−)-linalool,10 yielded low selectivity in the cyclizations. In conclusion, we have described a two-step, diastereoselective synthesis of furanoid linalyl oxides using a Sharpless asymmetric dihydroxylation and a diastereoselective cyclization using palladium and C3-TunePhos.

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