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Paper | Regular issue | Vol 89, No. 3, 2014, pp.679-691
Published online, 29th January, 2014
DOI: 10.3987/COM-14-12930
Synthesis of the Precursors of Pumiliotoxin 251D and Awajanomycin and Related Studies

Shang-Shing P. Chou,* Kuo-Shiun Yang, and Tzu-Han Chiu

*Department of Chemistry, Fu Jen Catholic University, 510 Chung-Cheng Rd., Hsin-Chuang, New Taipei City 24205, Taiwan, R.O.C.

Abstract

The aza-Diels–Alder reaction of 3-phenylthio-3-sulfolenes with p-toluenesulfonyl isocyanate (PTSI) gave trans-5,6-dihydropyridinones, which upon treatment with NBS afforded the trans-allylic bromides. Hydrolysis of the bromides provided the allylic alcohols with retention of configuration. Further synthetic transformations led to the formal synthesis of pumiliotoxin 251D and awajanomycin. Some related syntheses are also reported.