Facile One-Pot Epoxidation-Nucleophilic Opening Sequence for Vicinal Diols

An Efficient Formal Total Synthesis of Cladosporin

“…Selective Sharpless asymmetric dihydroxylation11 at the terminal double bond of cyclized product 6 was achieved by AD‐mix‐α to obtain diol 9 as a mixture of diastereomers [ dr ≈ 10:1, determined by HPLC] in 80 % yield. We proceeded onto the next step with this inseparable diasteromeric diol 9 , which was conveniently converted into epoxide 10 in 89 % yield by following the Forsyth protocol 12…”

Asymmetric synthesis of (−)-tetrahydrolipstatin

“…The alcohol 32 was more conveniently prepared in an one-pot operation following the Forsyth protocol. 24 Thus diol 29 on treatment with tosyl imidazole using sodium hydride as the base furnished epoxide 31, which without isolation was reacted with an excess of decylmagnesium bromide as before to furnish 32, Scheme 8.…”

Total Synthesis and Structural Assignment of Spongidepsin through a Stereodivergent Ring‐Closing‐Metathesis Strategy

“…The two enantiomers of syn ‐2,4‐dimethyl carboxylic acid 5 are derivable from acetate alcohol 7 by alternative manipulations of the terminal functional groups. Each of the four stereoisomers of 4 would originate from the known L ‐malate‐derived epoxide 6 , which bears a C9 stereogenic center 6…”