Synthesis of terprenin

This selectivity has been exploited in a synthesis of terprenin 2.26, an immunosuppressant compound (Scheme 2.10). The iodobromide 2.20 underwent selective Suzuki coupling with one boronic acid 2.21 at the iodo position, then a second boronic acid 2.23 at the bromo position. This two-step process could be carried out in one pot. The unusual catechol protecting group was not wasted, but converted into a prenyl ether at the end of the synthesis by hydrolysis and a Wittig reaction. 

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