Skip to main content
Skip to main menu Skip to spotlight region Skip to secondary region Skip to UGA region Skip to Tertiary region Skip to Quaternary region Skip to unit footer


Total Syntheses of Pepluanols A and B

Po-Sen Tseng
Po-Sen Tseng
Graduate Student, Department of Chemistry
University of Georgia
Chemistry Building, Room 400
Organic Seminar

Euphorbia is a large and diverse genus of flowering plants in the spurge family, comprising more than 2,000 species.1,2 Many of them have long been used in herbal folk medicine. In 2016 and 2018, Qiu and co-workers isolated five diterpenoids, pepluacetal and pepluanols A–D, from Euphorbia peplus.3,4 All five compounds show effective inhibitory activity on the KV1.3 voltage-gated potassium channel. Thus, they are potential candidates for the treatment of autoimmune diseases. To date, only three total syntheses have been published. Ding and co-workers reported the first total synthesis of (±)-pepluanol A in 2017.5 They completed the synthesis of this tetracyclic compound using Diels–Alder reaction, reductive annulation and Dauben–Michno reaction. In 2020, She research group published the first total synthesis of pepluanol B in both racemic and enantioenriched forms.6 A ring-closing metathesis was employed to construct the eight-member ring. The ring conformation was then controlled by a bromo-epoxidation to facilitate the following methylation with the desired configuration. In 2021, Gaich and co-workers completed a ten-step asymmetric total synthesis of (+)-pepluanol A.7 Their strategies included Nozaki–Hiyama–Kishi reaction and the Curtin–Hammett-driven stereo-convergent Diels–Alder reaction. All the chemistry in these three recently published articles will be presented in this seminar.

Pepluanol A and Pepluanol B illustration


  1. Shi, Q.-W.; Su, X.-H.; Kiyota, H. Chemical and Pharmacological Research of the Plants in Genus Euphorbia. Chem. Rev. 2008, 108, 4295–4327.
  2. Vasas, A.; Hohmann, J. Euphorbia Diterpenes: Isolation, Structure, Biological Activity, and Synthesis (2008–2012). Chem. Rev. 2014, 114, 8579–8679.
  3. Wan, L.-S.; Nian, Y.; Ye, C.-J.; Shao, L.-D.; Peng, X.-R.; Shao, L.- D.; Geng, C.-A.; Zuo, Z.-L.; Li, X.-N.; Yang, J.; Zhou, M.; Qiu, M.-H. Three Minor Diterpenoids with Three Carbon Skeletons from Euphorbia peplus. Org. Lett. 2016, 18, 2166–2169.
  4. Wan, L.-S.; Nian, Y.; Peng, X.-R.; Shao, L.-D.; Li, X.-N.; Yang, J.; Zhou, M.; Qiu, M.-H. Pepluanols C–D, Two Diterpenoids with Two Skeletons from Euphorbia peplus. Org. Lett. 2018, 20, 3074–3078.
  5. Xuan, J.; Liu, Z.; Zhu, A.; Rao, P.; Yu, L.; Ding, H. Diastereoselective Total Synthesis of the Euphorbia Diterpenoid Pepluanol A: A Reductive Annulation Approach. Angew. Chem. Int. Ed. 2017, 56, 8898–8901.
  6. Zhang, J.; Liu, M.; Wu, C.; Zhao, G.; Chen, P.; Zhou, L.; Xie, X.; Fang, R.; Li, H.; She, X. Total Synthesis of (–)-Pepluanol B: Conformational Control of the Eight-Membered-Ring System. Angew. Chem. Int. Ed. 2020, 59, 3966–3970.
  7. Yuan, P.; Gerlinger, C. K. G.; Herberger, J.; Gaich, T. Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A. J. Am. Chem. Soc. 2021, 143, 11934–11938.

Support Us

We appreciate your financial support. Your gift is important to us and helps support critical opportunities for students and faculty alike, including lectures, travel support, and any number of educational events that augment the classroom experience. Click here to learn more about giving.

Every dollar given has a direct impact upon our students and faculty.

Got More Questions?

Undergraduate inquiries: 

Registration and credit

AP Credit, Section Changes, Overrides,

Graduate inquiries:

Contact Us!

Assistant to the Department Head: Donna Spotts, 706-542-1919 

Main office phone: 706-542-1919 

Main Email:

Head of Chemistry: Prof. Jason Locklin