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. Author manuscript; available in PMC: 2014 Feb 6.
Published in final edited form as: J Am Chem Soc. 2013 Jan 28;135(5):1735–1738. doi: 10.1021/ja4001823

Table 1.

Summary of incorporation of partially assembled precursor analogues.

Intermediate Analoguea,b 13C Enrichment Relative RAL yieldc
0 none none observed 1.0
1 graphic file with name nihms440128t1.jpg 41% 0.4
2 graphic file with name nihms440128t2.jpg 37% 1.0
3 graphic file with name nihms440128t3.jpg 15% 0.6
4 graphic file with name nihms440128t4.jpg 78% 1.0
5 graphic file with name nihms440128t5.jpg 19% 0.4
6 graphic file with name nihms440128t6.jpg 27% 2.0
7 graphic file with name nihms440128t7.jpg 8% 0.9
8 graphic file with name nihms440128t8.jpg 39% 2.6
Unnatural analogued Productione Relative RAL yieldc
9 graphic file with name nihms440128t9.jpg 24% 1.3
10 graphic file with name nihms440128t10.jpg 25% 1.5
11 graphic file with name nihms440128t11.jpg 30% 2.0
12 graphic file with name nihms440128t12.jpg 0% 0.4
a

* indicates the location of 13C label;

b

ready precursor structures are shown in red;

c

resorcylic acid lactone (RAL) relative yield includes DHZ, and for unnatural precursor analogs, also the amount of corresponding DHZ analogs;

d

Compounds 912 have incorrect stereochemistry or functionality for conversion to DHZ and are therefore (except for 12) transformed to corresponding DHZ analogs;

e

production is the amount of DHZ analog formed compared to the total RAL production.