A. Synthetic strategy to access polysin, N-acetyl-polyveoline and the chrodrimanins from 9, which could be obtained via C9 epimerization of sclareolide (7). B. Screening of P450BM3 variants in our collection for the C3 hydroxylation of 9. C. Screening of P450BM3 variants in our collection for the C3 hydroxylation of 12. See Supporting Information for the identities of the variants tested. Reaction conditions for enzymatic hydroxylation were: 9 or 12 (5.0 mM), NADP + (1.0 mM), NaHPO3 (100 mM), clarified lysate of E. coli BL21(DE3) expressing the appropriate P450BM3 variant and Opt13 (suspension in 50 mM kPi (pH 8.0) and pre-lysis at an optical density of 30, measured at a wavelength of 600 nm) for 20 h at 20 °C. *additional regioisomers were detected in the product mixture.