Abstract
A stereoselective route to the C13–C28 subunit of (–)-laulimalide is described. l -Tartaric acid is the source of the hydroxy groups at C19 and C20. An α-chlorosulfide is employed as the key intermediate for the creation of the C17–C18 bond and the C16–C17 double bond was introduced using the Mislow–Braverman rearrangement and Hutchin’s dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans -disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia–Kocienski olefination reaction, respectively.
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