Biomimetic synthesis of myrtucommulone K, N and O

Recent trends in the structural revision of natural products

“…Recently, a biomimetic synthesis of 38 was reported with agreement between NMR spectroscopic and X-ray crystallographic data of synthetic and natural 38b . 103 Some originally reported HMBC correlations cannot be rationalized in light of the new structure since the hydrogens and the carbons are separated by 4–6 bonds. 101 However, due to the wide spectral window necessary to record a full HMBC spectrum for this compound (0-220 ppm in the indirect dimension), it is likely that the resulting low resolution led to confusion in the assignment of carbons with similar chemical shifts (Fig.…”

Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E

“…The synthetically challenging structural motifs of these PPPs together with their promising pharmacological properties have attracted considerable interest from the synthetic community. 5 , 6 In 2010, Jauch et al reported the first total synthesis of myrtucommulone A ( 1 ). 5 a However, the asymmetric total syntheses of compounds 2–7 are yet to be reported and the catalytic asymmetric and divergent syntheses of PPPs have not been achieved.…”

Biomimetic Synthesis of Psiguajdianone Guided Discovery of the Meroterpenoids from Psidium guajava

“…As a continuation of our interest in the biomimetic synthesis of caryophyllene meroterpenoids, we carried out a total synthesis to confirm the intriguing molecular architecture of 1 . Our synthetic strategy involves biomimetic cascade Knoevenagel condensation/hetero-Diels–Alder reaction followed by free radical dimerization.…”

“…As far as we know, this is the first meroterpenoid dimer coupling with a C− C bond, which is different from diguajadial, a meroterpenoid dimer coupling in a C−O−C bond from the same plant. 6 As a continuation of our interest in the biomimetic synthesis of caryophyllene meroterpenoids, 5 we carried out a total synthesis to confirm the intriguing molecular architecture of 1.…”