4.7 Article

Synthetic Efforts and Ultimate Limitation to an Asymmetric Achmatowicz Approach Toward EBC-23

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JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 9, 页码 6006-6013

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00262

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资金

  1. NIH [AI142040, AI154860]
  2. NSF [CHE-2102649]

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An asymmetric approach for the total synthesis of the polyketide natural product EBC-23 is reported, involving a convergent strategy and a late-stage Claisen-like enolate/acid chloride coupling. The key 1,3-diketone intermediate was successfully established, and further transformations led to the synthesis of EBC-23.
An effort toward the total synthesis of the polyketide natural product EBC-23 is reported. The asymmetric approach is convergent and uses a late-stage Claisen-like enolate/acid chloride coupling to establish a key 1,3-diketone intermediate. The 1,3-diketone target is an oxidized form of the hydrated natural product, which fails to spiroketalize. The convergent asymmetric synthesis uses an asymmetric Noyori transfer hydrogenation of a beta-furyl ketoester to enantioselectively form a chiral furyl alcohol. An Achmatowicz/Jones/Luche three-step reaction sequence was used to stereoselectively convert the furyl alcohol into the 5-hydroxy-pyran-2-one. The absolute stereochemistry of the 1,3-polyol fragment was established by a Leighton allylation. A subsequent Grubbs cross-metathesis, and Evans acetalation were used to install the 1,3-syn-diol stereochemistry.

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