Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B

Ming Zhong Wang*, Tong Xu Si, Chuen Fai KU, Hongjie ZHANG, Zheng Ming Li, Albert S C Chan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Javanicunines A-B and 9-deoxy-PF1233s A-B belong to a family of natural diketomorpholines with a unique isopropenyl group at C-10b or C-5a and a hydroxyl group at C-11a or C-10b. We herein reported the first total synthesis of javanicunines A-B and 9-deoxy-PF1233s A-B. Pivotal features of the synthesis included a nucleophilic substitution reaction, followed by a Davis' oxaziridine oxidation to assemble javanicunines A-B, and a chemoselective and stereoselective oxidation with Murray's reagent to install the requisite C-10b hydroxyl group in 9-deoxy-PF1233s A-B. The present synthesis also established the absolute configuration of javanicunine B.

Original languageEnglish
Pages (from-to)831-839
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number2
DOIs
Publication statusPublished - 18 Jan 2019

Scopus Subject Areas

  • Organic Chemistry

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