Isolation and biomimetic synthesis of (±)-calliviminones A and B, two novel Diels–Alder adducts, from Callistemon viminalis. Issue 1 (1st January 2015)

• Record Type: Journal Article
• Authors: Wu, Lin; Luo, Jun; Zhang, Yalong; Zhu, Mengdi; Wang, Xiaobing; Luo, Jianguang; Yang, Minghua; Yu, Boyang; Yao, Hequan; Dai, Yue; Guo, Qinglong; Chen, Yijun; Sun, Hongbin; Kong, Lingyi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 1(2015)
• Page Start: 229
• Page End: 232
• Publication Date: 2015-01-01
• Subjects: XUNKZDFPSKJKIN-GOSISDBHSA-N -- YZTHBNWXMOAWGE-GOSISDBHSA-N; β-Triketones -- Diels–Alder reaction -- Biomimetic synthesis -- Spiro compounds; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.11.075
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: (±)-Calliviminones A (1 ) and B (2 ), two Diels–Alder adducts of polymethylated phloroglucinol and myrcene with unprecedented spiro-[5.5] undecene skeleton, were isolated from the fruits of Callistemon viminalis . Structural elucidation was accomplished by NMR spectra studies, and the biomimetic synthesis of compounds1 and2 confirmed the pivotal role of Diels–Alder reaction in the plausible biosynthetic pathway. Compounds1 and2 were also the first example of Carbon Diels–Alder adducts between phloroglucinol and terpene. Bioactivity scan indicated that1 and2 showed moderate inhibition on NO production on lipopolysaccharide-induced RAW264.7 macrophages.