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Issue 28, 2019
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Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson–Khand reaction based one-stop synthetic solution

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Abstract

A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson–Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3–5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A.

Graphical abstract: Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson–Khand reaction based one-stop synthetic solution

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Publication details

The article was received on 13 Apr 2019, accepted on 20 Jun 2019 and first published on 20 Jun 2019


Article type: Paper
DOI: 10.1039/C9OB00855A
Org. Biomol. Chem., 2019,17, 6831-6842

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    Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson–Khand reaction based one-stop synthetic solution

    A. Salam, S. Ray, Md. A. Zaid, D. Kumar and T. Khan, Org. Biomol. Chem., 2019, 17, 6831
    DOI: 10.1039/C9OB00855A

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