Synthesis of the Proposed Structure of Mohangic Acid C

Takahashi, Keisuke; Kudo, Shunya; Kawamura, Kiharu; Kusakabe, Taichi; Kikkawa, Shoko; Azumaya, Isao; Kato, Kanefusa

doi:10.1021/acs.orglett.2c01285

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2024

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“…Mohangic acid E ( 5 ) showed potential quinone reductase (QR) activity [4] . Takahashi and coworkers [6] reported an elegant route for the first total synthesis of the proposed structure of mohangic acid C, one of the members of this family, where Stille cross coupling was adopted to install the triene moiety. A mismatch in NMR data of this target was observed with respect to the reported values of the isolated natural product.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Key Skeleton of Mohangic Acids A‐E

Mondal,

Guchhait,

Sharma

et al. 2024

Eur J Org Chem

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The key skeleton that could allow to access structurally intriguing mohangic acids A‐E has been synthesized in stereoselective manner. The salient features of this synthesis include Evans syn‐aldol reaction to construct the C‐11 and C‐12 centers, HWE olefination to construct C14‐C15 bond, Evans asymmetric methylation to install C‐14 center and Crimmins acetate aldol to generate C‐15 center whereas Wittig and Takai olefinations to prepare the C8‐C9 & C6‐C7 alkenes, respectively, and Heck reaction to couple C1‐C5 & C6‐C17 segments of the molecules. The developed route is highly modular and useful for accessing diverse natural product like molecules for future investigations

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Section: Introductionmentioning

confidence: 99%