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. Author manuscript; available in PMC: 2020 Apr 21.
Published in final edited form as: Chem Commun (Camb). 2019 Dec 17;56(1):157–160. doi: 10.1039/c9cc07966a

Fig. 2.

Fig. 2

(A) The relative configurations of the triketide stereoisomers can be readily assigned using Hoffmann’s method of summing the 13C NMR shifts for the C3 and C5 signals: the anti-isomers (e.g., 9ba) give a smaller δ(C3) + δ(C5) value than syn-isomers (e.g., 9aa) due to axial substituents on the chair formed by the hydroxyl and the methoxy groups. (B) Chiral chromatography of chemoenzymatically-generated triketides 8aa, 8ab, 8ba, and 8bb using two systems: an OC-H column coupled with a UV detector (left) and an IF3 column coupled with a time-of-flight mass spectrometer (right). The OC-H column was able to resolve the syn-products, while the IF3 column was able to resolve the anti-products. Retention times matched those of standards (Tables S1 and S2, ESI†).