The total synthesis of (-)-sigillin A, a highly chlorinated and oxygenated octahydroisocoumarin, is described herein. A hexahydroisocoumarin skeleton was constructed from ()-4-(trichloromethyl)oxetan-2-one in seven steps. Its unique manganese oxidation provided an enone as the key intermediate of sigillin A. Stereoselective installation of two hydroxy groups and formation of -dichloroalkene from the corresponding ketone led to the total synthesis of (-)-sigillin A in a total of 16 steps.
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