Zoapatanol and montanol, novel oxepane diterpenoids, from the Mexican plant zoapatle (Montanoa tomentosa)

Total Synthesis of (+)‐(2′S,3′R)‐Zoapatanol Exploiting the B‐Alkyl Suzuki Reaction and the Nucleophilic Potential of the Sulfinyl Group

“…Treatment22 of 32 with prenyllithium23 using Cossy’s method5b,c gave (+)‐zoapatanol by concomitant deacetylation in 72 % yield. The physical characteristics of the synthetic sample were in excellent agreement with those reported in the literature 1. 5a, c…”

“…Zoapatanol 1 is among the many diterpenoid oxepanes isolated1 from the leaves of the plant Montanoa tomentosa , which Mexican women use to prepare “tea” to induce menses and labor, and to terminate early pregnancy 2 Investigators have also suggested a potential use of zoapatanol and its bicyclic analogues as anti‐fertility agents 3.…”

Rare, seven-membered cyclic ether labdane diterpenoid from Dodonaea polyandra

“…To our knowledge only two instances exist in the literature of compounds with a similar 7-membered ring system, being that of a synthetically produced compound (Grant et al, 1975) and a halogenated marine natural product (Iliopoulou et al, 2003). Other examples of diterpenoids containing a 7-membered ether ring (not fused) include the oxepane diterpenoids zoapatanol and montanol (Levine et al, 1979).…”

Studies Towards the Synthesis of Aplykurodins - Synthesis of 17,18-Dihydro-3,9-di-epi-aplykurodinone B

“…The α-face diastereopreference, better than that observed in the case of incisterol synthesis, [3] was attributed to the presence of the OMEM and C-12 angular methyl groups. Acid-free AdamЈs reduction [17] afforded the stable allylic diol 26, whose 1 H-NMR spectrum showed a broad singlet at δ ϭ 4.73 for the C-4 methine proton, suggesting a quasi-axial orientation of the hydroxy group. Moreover, the chemical shift values of the C-1ϪC-4 protons were in good agreement with those of an intermediate prepared during the synthesis of (17R)-17-methylincisterol.…”