Journal of Organic Chemistry p. 1703 - 1708 (1994)
Update date:2022-07-30
Topics:
Marshall, James A.
DuBay, William J.
The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a "furan last" approach.The former was obtained in 64percent yield upon treatment of the 12-membered β-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH.The latter was formed in 88percent yield from the 14-membered γ-alkynyl allylic alcohol 25 under comparable conditions.The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horney-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.
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