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. Author manuscript; available in PMC: 2014 Jun 24.
Published in final edited form as: Tetrahedron. 2013 Apr 15;69(25):5205–5220. doi: 10.1016/j.tet.2013.04.041

Scheme 22.

Scheme 22

Fragment coupling to access the backbone of armatol A. Reagents and conditions: a) (i) [Cp2Zr(H)Cl], CH2Cl2, rt; (ii) Me2Zn, CH2Cl2, −78 °C; (iii) 78, CH2Cl2, −78 °C to rt, 64%; b) H2 (1 atm), Pd/C, EtOH, rt; c) TPAP, NMO, 4ÅMS, CH2Cl2, 0 °C to rt, 53% (from 87); d) (i) [Cp2Zr(H)Cl], CH2Cl2, rt; (ii) Me2Zn, CH2Cl2, −78 °C; (iii) ent-78, CH2Cl2, −78 °C to rt; e) H2 (1 atm), Pd/C, EtOH, rt, 52% (from ent-78); f) TPAP, NMO, 4Å MS, CH2Cl2, 0 °C to rt, 90%.