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Org. Process Res. Dev. 2024, 28, 1078 − 1082. DOI: 10.1021/acs.oprd.3c00472 ◆ The disclosed synthesis of 10 used
5-chloro-2-bromopyridine and trimethylsilylacetylene to form
5-chloro-2-ethynylpyridine, which was further reacted with 3-bromocatechol 2
and Ru3(CO)10 to form acetal 10 in 3 overall steps. ◆ One successful strategy involved
construction of the pyridine ring in 10 from chiral ketone 1. ◆ While (trans)ketalizations alongside
several alternative strategies were unsuccessful, a double nucleophilic substitution
approach emerged as the lead option ◆ The lack of reactivity of 2 with ketone 3a
was hence attributed to its inability to form an alpha-lactone . ◆ We leveraged our High-Throughput
Experimentation (HTE) capabilities to further explore this reaction. ◆ Despite observations of its limited
solubility in heptane, attempts to purify 4 with trituration or
recrystallization were unsuccessful, prompting exploration of its isolation as
a salt. ◆ Several methods we
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