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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 16 — Synthesis of β-lactone 79.^a

^a Reagents and conditions: (a) 2.0 equiv. (COCl)₂, 4.0 equiv. DMSO, 4.6 equiv. Et₃N, CH₂Cl₂, −78 °C to 0 °C. (b) 1.0 equiv. Me₂AlCl, 1.1 equiv. 80, CH₂Cl₂, −78 °C, 0.5 h. (c) 1.5 equiv. KF.2H₂O, CH₃CN, 25 °C, 1 h, then 40% aq. HF, 0 °C, 0.5 h, 69% (3 steps), d.r. 1.6:1.