4.5 Article

Protecting-Group-Free Total Synthesis of (-)-Boscartin A in 3 Steps from (-)-Boscartin F via Wharton Reaction

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 47, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201366

Keywords

boscartin A; enantioselective; protecting-group-free; total synthesis; Wharton reaction

Funding

  1. JSPS KAKENHI [JP16K08180, JP18K14876, JP19K06981, JP21K14797]
  2. Sumitomo Foundation [2200155]

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In this report, the first total synthesis of (-)-boscartin A, a cembranoid with a 5/5/12-fused tricyclic structure, was described. (-)-Boscartin A was obtained in three steps from (-)-boscartin F, with an overall yield of 46%, utilizing key reactions including stereoselective epoxidation and Wharton reaction.
In this report, we described the first total synthesis of (-)-boscartin A, a cembranoid featuring a 5/5/12-fused tricyclic structure. Via the key reactions, including stereoselective epoxidation and Wharton reaction, (-)-Boscartin A was obtained in three steps from (-)-boscartin F, with 46 % overall yield.

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