A new, iterative strategy for the synthesis of unsymmetrical polyynes: application to the total synthesis of 15,16-dihydrominquartynoic acid

Organic Letters
Sanghee KimDeukjoon Kim

Abstract

[reaction: see text] A new iterative strategy for the synthesis of unsymmetrically substituted polyynes has been developed. The starting bromoalkyne is homologated by one acetylene unit through palladium-catalyzed cross-coupling with a TIPS-protected terminal acetylene and a subsequent in situ one-pot AgF-mediated desilylative bromination. The utility of this new synthetic method is demonstrated by its application to the total synthesis of (S)-(E)-15,16-dihydrominquartynoic acid.

References

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Citations

Mar 21, 2013·Nature Chemistry·Tobias N HoheiselHolger Frauenrath
May 2, 2007·Chemical Society Reviews·Ulla Halbes-LetinoisPatrick Pale
Dec 5, 2012·Beilstein Journal of Organic Chemistry·Andrew Tigchelaar, William Tam
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Oct 8, 2016·Organic & Biomolecular Chemistry·Tapan Kumar Kuilya, Rajib Kumar Goswami
Sep 26, 2007·Angewandte Chemie·Seonwoo LeeSanghee Kim
Feb 1, 2006·Angewandte Chemie·Annabelle L K Shi Shun, Rik R Tykwinski
Jan 1, 2015·Chemical Science·Stephen SchrettlHolger Frauenrath
Sep 25, 2008·Organic Letters·Tobias N Hoheisel, Holger Frauenrath
Nov 15, 2008·The Journal of Organic Chemistry·Masaru Okutani, Yuji Mori
Nov 15, 2007·The Journal of Organic Chemistry·Jean-François MorinJames M Tour
Sep 3, 2010·The Journal of Organic Chemistry·Zhengwang ChenShaorong Yang
Dec 16, 2005·Organic Letters·Woo-Jin YooWilliam Tam

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