Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6761-6764Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02391
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Funding
- High End Talent Program of Yunnan Province [2015HA028]
- NSFC [21372229]
- 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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