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. Author manuscript; available in PMC: 2009 Oct 6.
Published in final edited form as: Tetrahedron Lett. 2008 Oct 6;49(41):5931–5934. doi: 10.1016/j.tetlet.2008.07.155

Scheme 4.

Scheme 4

Conditions to obtain macrocyclic diketone 14, tricyclic ketones 15/16, and tetracyclic diene 17

Key: Reagents and conditions: a) DMDO, acetone, CH2Cl2, 2h, 83%; b) PtCl2, toluene, 80%; c) 10% Pd(OAc)2, 5 eq. LiBr, 2 eq. Cu(OAc)2, 1.2 eq. K2CO3, CH3CN, 37%.