Synthesis of various secosteroidal macrocycles by ring-closing metathesis

• An efficient synthesis of 7,8- and 12,13-secosteroids possessing a macrocycle is described.
• The key steps are a ring-opening sequence and a ring-closing metathesis reaction.
• The ring size of the macrocycle can be modified efficiently.

We set out to describe an efficient and versatile method for preparing secosteroidal macrocycles from cholic acid, via an oxidative ring-expansion/ring-opening sequence and a ring-closing metathesis reaction as the key steps. The characteristic 1H and 13C NMR spectroscopic features of the synthesized compounds are reported.

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