The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of
12.6%. The absolute stereochemistry of the C4−C12, C33−C38, and C13−C19 fragments was established utilizing
catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20−C32 fragment was
derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through
internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl
glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated
oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully
elaborated alkenyl metal side chain.
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