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. 2019 May 28;20(11):2627. doi: 10.3390/ijms20112627

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© 2019 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 9 — Attempted approach via 8(9)-podocarpen-14-one 46. Reagents and conditions: (a) (1) TsNHNH₂, THF, reflux, 3 h; (2) NaBH₃CN, reflux, 8 h (b) (1) NaH, THF, reflux, 1 h; (2) BnBr, reflux, 3 h (c) 2N HCl, reflux, 30 min (d) (1) BrMgCHCH₂, THF, 0 °C, N₂; (2) PBr₃, CH₂Cl₂, dimethylformamide, −10 °C, N₂; 3 h 0 °C.; (e) α-acetoxycrilonitrile, Carius tube, 110 °C, N₂, 3 d; (f) allene, hν, pyrex, −78 °C; (g) ethylene glycol, TsOH, benzene, Dean–Stark; and (h) OsO₄/NaIO₄.