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. Author manuscript; available in PMC: 2021 Nov 11.
Published in final edited form as: J Org Chem. 2021 Jul 13;86(15):10249–10262. doi: 10.1021/acs.joc.1c00985

Scheme 1. Synthesis of key intermediate 9 from testosterone.

Scheme 1.

a) LDA, THF, −78 °C then TMSCl; b) Pd(OAc)2, MeCN, r.t., 65% yield, 2 steps; c) SiO2, DIPEA, toluene, 60 °C; 69% yield (95% BRSM).