Four Polyoxygenated Cyclohexenes from the Chinese Tree, Uvaria purpurea

Polyoxygenated Cyclohexenes from the Chinese Tree,Uvaria Purpurea

“…The absolute stereochemistry of 4 had been deduced in a previous paper 9) to be of (1R, 2S, 3R) form from the CD spectrum and large negative Cotton eŠect. The absolute stereochemistry of 5 and 6 were also established from their CD spectra.…”

Photooxygenation of a Microbial Arene Oxidation Product and Regioselective Kornblum–DeLaMare Rearrangement: Total Synthesis of Zeylenols and Zeylenones

“…Thus, uvarigranol C (−)‐ 4 is enantiomeric with uvaribonol C (+)‐ 4 and uvarigranol F (+)‐ 7 is enantiomeric with uvaribonol A (−)‐ 7 ; the reported optical rotations are in good agreement and of opposite sign. For compounds where the absolute configuration has not yet been established, caution must be exercised in inferring configuration from the structures of known co‐isolates, since polyoxygenated cyclohexenes in both enantiomeric series have been isolated from the same organism 3f. g, 7b, 9b, 10…”

“…In terms of biological activity, (−)‐ 1 has been studied most extensively, and shows antitumour9a, 17 and antifeedant activity 13. Furthermore, (−)‐ 1 affects root and shoot growth of Lactuca sativa (as do compounds 11 , 17 and 18 ) 3f,g. In contrast, the antipodal (+)‐ 1 shows selective cytotoxicity towards HL‐60 leukaemia cells 6c.…”

Crystal structure of 5-[(benzoyloxy)methyl]-5,6-dihydroxy-4-oxocyclohex-2-en-1-yl benzoate

“…The biological activity of zeylenone was reported as inducing apoptosis in the mitochondria of gastric cancer cells (Yang et al, 2018) and cervical carcinoma cells (Zhang et al, 2017). The absolute configuration of natural zeylenone was determined by CD spectroscopy to be (À)-zeylenone (Takeuchi et al, 2001).…”