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Issue 10, 2018
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Total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethyl-octahydro-naphthalene-1,4a(2H)-diol

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Abstract

The first total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethylocta-hydronaphthalene-1,4a(2H)-diol (1), a degraded sesquiterpene isolated from a fermentation broth of Streptomyces albolongus, has been achieved via three different synthetic approaches (13–15 steps) starting from racemic Wieland–Miescher ketone (2). The configuration of hydroxyl groups at C-1 and C-4a in 1 was availably managed using the Mitsunobu reaction and stereo- and regioselective epoxidation. Moreover, the syntheses of configuration isomers 12, 17, 45 and 54 were also described in the present study.

Graphical abstract: Total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethyl-octahydro-naphthalene-1,4a(2H)-diol

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Publication details

The article was received on 02 Mar 2018, accepted on 03 Apr 2018 and first published on 04 Apr 2018


Article type: Research Article
DOI: 10.1039/C8QO00225H
Citation: Org. Chem. Front., 2018,5, 1719-1723
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    Total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethyl-octahydro-naphthalene-1,4a(2H)-diol

    Q. Liu, L. Han, B. Qin, Y. Mu, P. Guan, S. Wang and X. Huang, Org. Chem. Front., 2018, 5, 1719
    DOI: 10.1039/C8QO00225H

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