4.8 Article

Total Synthesis of (±)-Cochlearol A

Journal

ORGANIC LETTERS
Volume 21, Issue 17, Pages 6761-6764

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02391

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Funding

  1. High End Talent Program of Yunnan Province [2015HA028]
  2. NSFC [21372229]
  3. Hundred-Talent Program of KMU

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Total synthesis of (+/-)-cochlearol A was accomplished, which features a cis 6/6 B/D ring synthesis. A TMSOTf-promoted lactonization of tert-butoxy ketoester produced the desired lactone with quaternary carbon. The cis configuration of the B/E ring is essential for regioselective B/D ring formation. Finally, simple deprotections and trans- formations gave cochlearol A in 16 steps from known ethyl 4-tert-butoxyacetoacetate.

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