Enantioselective total synthesis of (-)-dactylolide

Organic Letters
Ignace LouisMalcolm D McLeod

Abstract

[reaction: see text] The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.

References

Dec 6, 2001·Journal of the American Chemical Society·A B SmithR M Corbett
Dec 6, 2001·Journal of the American Chemical Society·T A KirklandS F Martin
Feb 15, 2002·Organic Letters·Amos B Smith, Igor G Safonov
Sep 13, 2002·Journal of the American Chemical Society·Amos B SmithR Michael Corbett
Aug 9, 2003·Journal of the American Chemical Society·Thomas R Hoye, Min Hu
Oct 11, 2003·Organic Letters·Eriks Rozners, Qun Xu
Jun 10, 2004·Chemical Reviews·Ana M Martín Castro
Jun 4, 2005·Organic Letters·Fei Ding, Michael P Jennings
Jul 1, 2005·Organic Letters·Carina C Sanchez, Gary E Keck
Oct 14, 2005·Journal of the American Chemical Society·Gregory HughesStephen L Buchwald

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Citations

Nov 17, 2011·Organic Letters·Patrick G McGarraugh, Stacey E Brenner-Moyer
Jun 23, 2012·Organic Letters·Matthew R Wilson, Richard E Taylor
Feb 6, 2008·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
May 28, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xufen Yu, Dianqing Sun
Jun 20, 2014·Natural Product Reports·Qiao-Hong Chen, David G I Kingston
Sep 25, 2007·Chemistry, an Asian Journal·Tracy Yuen Sze But, Patrick H Toy
Aug 4, 2008·Advanced Synthesis & Catalysis·Dawn M TroastJohn A Porco
Jan 29, 2009·Journal of Separation Science·Daniel Anthony Dias, Sylvia Urban
May 12, 2010·Angewandte Chemie·Sang Young YunDaesung Lee
Jan 12, 2013·Chembiochem : a European Journal of Chemical Biology·Asifa MunawarColin M Lazarus
Nov 9, 2012·Chemistry : a European Journal·Didier ZurwerraKarl-Heinz Altmann
Jan 13, 2011·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
Apr 23, 2009·Chemical Reviews·K C Kumara SwamyK V P Pavan Kumar
Apr 27, 2010·Organic Letters·Didier ZurwerraKarl-Heinz Altmann
Jun 9, 2011·Organic Letters·Ivan VolchkovDaesung Lee

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