Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2022; 18(06): 0581
DOI: 10.1055/s-0041-1738194
DOI: 10.1055/s-0041-1738194
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (–)-Grayanotoxin III
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
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.
#
#
Publication History
Article published online:
17 May 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany