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. 2020 Oct 1;25(19):4510. doi: 10.3390/molecules25194510

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© 2020 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 1 — Reagents and conditions: (i) 4 (1 equiv), DIBALH (2.4 equiv), dry toluene, −78 °C; (ii) 5 (1 equiv), NaSEt (4 equiv), dry DMF, 110 °C; (iii) 4 (1 equiv), morpholine (2 equiv), DIBALH (1 equiv), dry THF, 0 °C; (iv) 7 (1 equiv), corresponding organolithium reagent (2 equiv), dry THF, 0 °C or −78 °C depending on the organolithium reagent; (v) PBr₃ (0.34 equiv), LiI (3 equiv), dry CH₂Cl₂, rt; (vi) TBAF (2 equiv), THF, rt; (vii) 4 (1 equiv), organolithium reagent (4 equiv), dry THF, 0 °C or −78 °C depending on the organolithium reagent; (viii) 6 (1 equiv), HI (10 equiv), MeCN, rt; (ix) TBAF (1.1 equiv), THF, rt.