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Issue 15, 2013
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Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction

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Abstract

Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno–Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno–Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.

Graphical abstract: Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction

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Publication details

The article was received on 10 Jan 2013, accepted on 11 Feb 2013 and first published on 12 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB00053B
Org. Biomol. Chem., 2013,11, 2498-2513

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    Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction

    J. Zhang, C. Yan, Y. Peng, Z. Luo, X. Xu and Y. Wang, Org. Biomol. Chem., 2013, 11, 2498
    DOI: 10.1039/C3OB00053B

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