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Issue 32, 2019
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Bio-inspired enantioselective total syntheses of (−)-viminalins A, B, H, I, and N and structural reassignment of (−)-viminalin M

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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.

Graphical abstract: Bio-inspired enantioselective total syntheses of (−)-viminalins A, B, H, I, and N and structural reassignment of (−)-viminalin M

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Publication details

The article was received on 25 Jun 2019, accepted on 15 Jul 2019 and first published on 16 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01426H
Org. Biomol. Chem., 2019,17, 7507-7516

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    Bio-inspired enantioselective total syntheses of (−)-viminalins A, B, H, I, and N and structural reassignment of (−)-viminalin M

    D. H. Dethe and A. K. Nirpal, Org. Biomol. Chem., 2019, 17, 7507
    DOI: 10.1039/C9OB01426H

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