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Total Synthesis of (+)-Oocydin A: Application of the Suzuki–Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl 9-BBN


  • Financial support from the Institut de Chimie des Substances Naturelles, CNRS is acknowledged. 9-BBN=9-borabicyclo[3.3.1]nonane.


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Two sensitive fragments were coupled in the mild title reaction to create the Z-chlorovinyl functionality of the target macrolide oocydin A (1; see scheme). Another highlight in the total synthesis of 1 was an efficient stereoselective Pd0-catalyzed cyclization to form the highly substituted tetrahydrofuran ring. Bz=benzoyl, TBS=tert-butyldimethylsilyl, MPM=4-methoxyphenylmethyl.