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Total Synthesis of (−)-Sigillin A: A Polychlorinated and Polyoxygenated Natural Product

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journal contribution
posted on 16.09.2020, 14:07 by Yousuke Yamaoka, Takamori Nakayama, Shota Kawai, Kiyosei Takasu
The total synthesis of (−)-sigillin A, a highly chlorinated and oxygenated octahydroisocoumarin, is described herein. A hexahydroisocoumarin skeleton was constructed from (R)-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 gem-dichloroalkene from the corresponding ketone led to the total synthesis of (−)-sigillin A in a total of 16 steps.