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. Author manuscript; available in PMC: 2008 Jun 25.
Published in final edited form as: Tetrahedron. 2007 Jun 25;63(26):5768–5796. doi: 10.1016/j.tet.2007.02.058

Table 1. Attempted esterification reactions.

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entry reaction conditions Results
1 27 + 13 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, THF, rt to reflux decomposition of acid
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2 27 + 13 EDCI•MeI, DMAP, CH2Cl2, 0 to 23 °C
3 28 + 13 PyBrOP, i-Pr2NEt, CH2Cl2, 0 to 23 °C
4 28 + 33 Tol., 23 to 100 °C
5 28 + 31 30 (10 mol %), Tol., 50 °C
6 29 + 13 DCC, HOBt, THF, 23 to 50 °C
7 29 + 32 29, (Bu3Sn)2O, PhH, reflux; then add 32, CH2Cl2
8 29 + 32 29, LDA, −78 °C, THF; then 32 or 33, THF
9 25 + 13 13, HCCOEt, {RuCl2(p-cymene)}2, PhMe, 0 to 23°C; then add 25, CSA (10 mol %), PhMe, 50 °C