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. Author manuscript; available in PMC: 2017 Mar 17.
Published in final edited form as: J Am Chem Soc. 2011 Jan 31;133(19):7260–7263. doi: 10.1021/ja200034b

Scheme 2. (a) Dimerization of the exo-Mesityl Diazofluorene 18,a (b) Stereochemical Model for the Dimerization Event, and (c) Cyclization of the Ketone Isomer (25) of Lomaiviticin Aglycon (3).

Scheme 2

aConditions: (a) TMSOTf, Et3N, CH2Cl2, 0 °C, then 21, PhH, 21 °C, 26% 22, 12% 23, 30% 18. (b) TFA, TBHP, CH2Cl2, −35 °C, 12 h, 39%. (c) TFA, CH3OH, 50 °C, 41%.