4.8 Article

Seven-Step Stereodivergent Total Syntheses of Punicafolin and Macaranganin

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 3, Pages 1428-1434

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c10714

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Funding

  1. JSPS KAKENHI [JP26221301, JP18H04405]
  2. Kobayashi Foundation
  3. Naito Foundation

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The total syntheses of punicafolin and macaranganin were achieved in seven steps each, starting from commercial alpha-D-glucose. The key features include sequential site-selective introduction of galloyl groups and stereodivergent construction of the 3,6-HHDP bridge without using protective groups for glucose, resulting in extremely short-step syntheses of natural glycosides with a molecular weight of 938.
The first total syntheses of punicafolin (1) and macaranganin (2) were achieved in seven steps, respectively, from commercial alpha-D-glucose. The characteristic features of the synthesis are (1) sequential site-selective introduction of the adequate galloyl groups into unprotected D-glucose by a catalyst-controlled manner and (2) stereodivergent construction of the 3,6-HHDP bridge by oxidative phenol coupling of a common intermediate via a ring-flipping process of the glucose core. Because no protective groups were used for glucose throughout the process, extremely short-step total syntheses of natural glycosides 1 and 2 (MW 938) were performed.

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