Kong L,
Yu H,
Deng M,
Wu F,
Jiang Z,
Luo T.
*
Peking University, Beijing and Institute of Molecular Physiology, Shenzhen Bay Laboratory,
P. R. of China
Enantioselective Total Syntheses of Grayanane Diterpenoids: (–)-Grayanotoxin III,
(+)-Principinol E, and (–)-Rhodomollein XX.
J. Am. Chem. Soc. 2022;
144: 5268-5273
DOI:
10.1021/jacs.2c01692
Key words
(–)-grayanotoxin III - grayanane diterpenoids - Vilsmeier–Haack reaction - Mukaiyama
aldol addition - Hosomi–Sakurai reaction - Suzuki–Miyaura coupling - Schenck ene reaction
- Ir catalysis - deformylation -
1O Diels–Alder reaction
Significance
Luo and co-workers disclose an enantioselective convergent approach towards three
grayanane diterpenoids: (–)-grayanotoxin III, (+)‑principinol E, and (–)-rhodomollein
XX.
Comment
The convergent approach is made possible by assembling fragment B and C in a diastereoselective Mukaiyama aldol addition catalyzed by the chiral hydrogen
bond donor D.
