T. Shih, Wei-Lin Gao
Feb 18, 2013
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0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
Abstract Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11–12 steps starting from d -(−)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7 , 8 , and 18 – 21 by 1.0 M BCl 3 of CH 2 Cl 2 solution at −78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.