A retro-Claisen approach to dolabriferol

Organic Letters
Troy Lister, Michael V Perkins

Abstract

[reaction: see text] The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

References

Jun 13, 2002·Journal of the American Chemical Society·Karl A ScheidtWilliam R Roush

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Citations

Jul 14, 2016·Organic Letters·Athanasios KaragiannisDale E Ward
Oct 21, 2009·ChemSusChem·James H ClarkDuncan J Macquarrie
Mar 31, 2012·Angewandte Chemie·Russell H Currie, Jonathan M Goodman
Sep 25, 2010·Angewandte Chemie·Sylvain LaclefPierre Vogel
Jul 4, 2009·The Journal of Organic Chemistry·Luiz C Dias, Airton G Salles
May 4, 2021·Journal of the American Chemical Society·Bhavin V PipaliyaP Andrew Evans
Apr 9, 2011·Organic Letters·Lei WangTao Ye
Dec 15, 2018·Organic Letters·Stephan Scheeff, Dirk Menche
Dec 6, 2012·Organic Letters·Dale E Ward, M Mehdi Zahedi
Jan 12, 2011·The Journal of Organic Chemistry·Claudia J ExnerPierre Vogel
Oct 4, 2007·The Journal of Organic Chemistry·Nicholas PelchatRobert Chênevert

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