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

Published on 2020-09-16T14:07:40Z (GMT) by
The total synthesis of (−)-sigillin A, a highly chlorinated and oxygenated octahydroisocoumarin, is described herein. A hexahydroisocoumarin skeleton was constructed from (<i>R</i>)-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 <i>gem</i>-dichloroalkene from the corresponding ketone led to the total synthesis of (−)-sigillin A in a total of 16 steps.

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Yamaoka, Yousuke; Nakayama, Takamori; Kawai, Shota; Takasu, Kiyosei (2020): Total Synthesis of (−)-Sigillin A: A Polychlorinated

and Polyoxygenated Natural Product. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c02930