Terprenin

Terpinenes, teipinols see p-menthadienes. Terpinenols, a-terpimol see p-menthenols. o-Terpineol acetate see oil of cardamom. 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. 

---