4.7 Article

Synthesis of the Scalarane Sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 17, Pages 7216-7221

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2008127

Keywords

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Funding

  1. Shanghai Foundation of Science and Technology [09JC1404200]
  2. National High Technology Research and Development Program of China [2006AA09Z447, 2007AA02Z301, 2011AA-10A207]
  3. China 111 Project [B07023]

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The marine natural product 16-deacetoxy-12-epi-scalarafuranacetate, isolated from Spongua officinalis, was synthesized in 18 linear steps, starting from (-)-sclareol, with high stereoselectivity and an overall yield of 6.1%. The intermediate 16-deacetoxy-12-epi-scalarafuran could be easily transformed into a series of natural scalarane sesterterpenoids in a few steps.

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