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Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N and structural reassignment of
Dattatraya H Dethe1, Appasaheb K Nirpal1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. ddethe@iitk.ac.in.
Abstract:
Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N, isolated from the Myrtaceae family, were accomplished in a convergent fashion in 5, 5, 1, 1, and 3 steps, respectively. A highly regio- and diastereoselective oxidative [3 + 2] cycloaddition reaction of acylphloroglucinols with α-phellandrene, diastereoselective modified Friedel-Crafts reaction of acylphloroglucinols with piperetol, and stereoselective epoxidation of extremely hindered β-face were described as key reactions.
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