Isolation and structural elucidation of zoapatanol and montanol, novel oxepane diterpenoids from the Mexican plant zoapatle (Montanoa tomentosa)

Studies of Zoapatle I. The Extraction of Zoapatle (Montanoa tomentosa) and the Identification of 21-Normontanol as the Initial Decomposition Product of Zoapatanol

“…Thirdly, we have shown that zoapatanol should not be stored neat, but rather in an organic solvent at low temperature, and that 21-normontanol ( 2) is the primary decomposition product. These accumulated data lead us to suggest that zoapatanol may not be the sole agent responsible for the biological activities observed for the aqueous preparations of zoapatle leaves as has previously been reported (3,4,8,11).…”

“…A substantial number of papers and patents in the recent past have concerned the diterpene zoapatanol (1), one of the principles claimed to be responsible for the antiimplantation activity of the tea. The structure of 1 was established through X-ray crystallography of its tosylhydrazone derivative (3,4) and, subsequently, through total synthesis (5)(6)(7).…”

Asymmetric Synthesis of New Chiral Cyclic Ketols

“…To test the potential of these new synthons, we chose to prepare stereoisomeric cyclic ketols 3a − c from keto enol acetate 2a (Schemes and ). This kind of ketol has been used for the synthesis of bioactive compounds such as Zoapatanol 1 …”

Seven-Membered Ring Nucleoside Analogues: Stereoselective Synthesis and Studies on Their Conformational Properties

“…Seven-membered oxepane scaffolds are commonly found in natural products and biologically active molecules. − In the search for ring-expanded DNA analogues, we recently reported the synthesis of oligonucleotides constructed from oxepane nucleosides (oxepane nucleic acids, ONA, 2 ) . It was hypothesized that expanding the carbohydrate moiety of DNA to a seven-membered skeleton would provide conformationally more flexible sugars relative to the six-membered ring pyranose, thus better mimicking the conformation of natural 2-deoxyribose.…”