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. Author manuscript; available in PMC: 2008 Nov 20.
Published in final edited form as: J Med Chem. 2007 Jan 31;50(4):713–725. doi: 10.1021/jm061071x

Scheme 3. Synthesis of Baccatins 11a–da.

Scheme 3

a a. LHMDS,THF, 0 °C, acryloyl chloride (9a, 52%), 4-pentenoyl chloride (9b, 78%), 5-hexenoyl chloride (9c, 71%), 6-heptenoyl chloride (9d, 50%). b. i, HF.Py, THF (n = 0, 60%, n = 2, 91%, n = 3, 80%, n = 4, 44%). ii, CeCl3, Ac2O, THF (10a, n = 0, 89%), (10b, n = 2, 92%), (10c, n = 3, 89%), (10d, n = 4, 95%). c. Triethylsilyl chloride, imidazole, DMF (11a, n = 0, 87%), (11b, n = 2, 85%), (11c, n = 3, 72%), (11d, n = 4, 83%).