The complex macrolide apoptolidinone (1) was synthesized in 19 steps (longest linear sequence) from (S)-malic acid. Key reactions include A) two stereoselective aldol reactions, B) a late-stage Grubbs cross-metathesis reaction to install a trisubstituted vinyl boronate, and C) an intramolecular Suzuki–Miyaura reaction.
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Wu et al. (2004) studied this question.
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