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. 2020 Apr 7;16:628–637. doi: 10.3762/bjoc.16.59

Scheme 1.

Scheme 1

Reaction conditions: a) MeOH, H2SO4 (5 drops), MS 4 Å (2 pieces), 68 °C, 8 h, 81%; b) DIBAL-H (1.2 equiv), 6 h, −78 °C, THF, 78%; c) phosphorane 8 (2.0 equiv), THF, 8 h, 60 °C, 72%; d) SeO2, dioxane, 110 °C, 8 h, 61%; e) indolamine 10 (1.1 equiv) DCE, sodium triacetoxyborohydride (STAB, 1.1 equiv), TEA (2 equiv), rt, 63%; f) NaOH at −10 °C, NH2OH·H2O at −10 °C, MeOH , rt, 12 h, 55%.