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. Author manuscript; available in PMC: 2016 Oct 2.
Published in final edited form as: J Org Chem. 2015 Oct 2;80(19):9740–9766. doi: 10.1021/acs.joc.5b01844

Table 1.

Ireland–Claisen Screenings for D Ring Assembly

graphic file with name nihms725716u2.jpg
entry acid ester (yield)a acid (yield, dr)a
1 Ac2O 70a (82%)b --
2 graphic file with name nihms725716t1.jpg 70b (83%) --
3 graphic file with name nihms725716t2.jpg 70c (73%) 71a (80%, 6:1)c
4 graphic file with name nihms725716t3.jpg 70d (93%) --
5 graphic file with name nihms725716t4.jpg 70e (63%) --
6 graphic file with name nihms725716t5.jpg 70f (74%) --
7 graphic file with name nihms725716t6.jpg 70g (54%) --
8 graphic file with name nihms725716t7.jpg 70h (87%) 71b (57%, 6.6:1.1:1)c
a

Isolated yields.

b

Conditions: Ac2O, NEt3, DMAP (10 mol %), CH2Cl2, rt.

c

Determined by 1H NMR analysis of crude mixtures.