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. Author manuscript; available in PMC: 2008 Sep 11.
Published in final edited form as: J Am Chem Soc. 2005 Dec 21;127(50):17921–17937. doi: 10.1021/ja055967n

Scheme 17.

Scheme 17

Attempted formation of the amphidinolide 15-membered ring system.a

a Reagents and conditions: (a) 4.0 equiv. TBAF, THF, 0 °C, 5 h, 71%. (b) 0.1 equiv. 85, hexane, 0.001M, reflux, 20 min, quant.