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. 2019 Nov 26;11(1):65–71. doi: 10.1021/acsmedchemlett.9b00477

Scheme 1. Application of Olefin Metathesis to Obtain Diversely Substituted Long Chain Alkanes.

Scheme 1

Reagents and conditions: (a) Grubbs 1st gen. (0.02 equiv), reduced pressure up to 2 mbar, RT up to 50 °C; (b) Pd(OH)2 on C (20%; 0.2 equiv), H2, MeOH/EA (2:1), RT; (c) LiAlH4 2 M solution in THF (2.5 equiv), THF, reflux; (d) NBS (3.0 equiv), PPh3 (3.0 equiv), THF, RT; (e) HBr 48% solution in H2O (3.0 equiv), toluene, reflux; (f) furan (3.0 equiv), dioxane, 90 °C; (g) DIAD (1.3 equiv), PPh3 (1.3 equiv), THF, 0 °C to RT; (h) succinimide (1.5 equiv), K2CO3 (1.5 equiv), DMF, 60°C; (i) 7 (1.5 equiv), K2CO3, (1.5 equiv), DMF, 60 °C.