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. Author manuscript; available in PMC: 2020 Feb 20.
Published in final edited form as: J Am Chem Soc. 2019 Feb 11;141(7):3083–3099. doi: 10.1021/jacs.8b12247

Scheme 4.

Scheme 4.

Formal Synthesis of 11-O-Debenzoyltashironin (4) and 3,6-Dideoxy-10-Hydroxypseudoanisatin (72)a

aReagents and conditions: (a) TsOH•H2O (1.5 equiv), DCE, 60 °C, 10 h, 1:1.4 d.r.; (b) lithium naphthalenide (3.0 equiv), THF, –78 °C, 10 min, 74% (two steps), >20:1 d.r.; (c) [Fe(mep)(MeCN)2][(SbF6)2] (50 mol%), TBHP (3.0 equiv), MeCN, 1 h, 56% 69, 20% 70; (d) TMSCl (10.0 equiv), NaI (5.0 equiv), MeCN, 80 °C, 45 min, 46%.