Total synthesis of haterumalides NA and NC via a chromium-mediated macrocyclization.

Journal of the American Chemical Society
Jennifer M Schomaker, Babak Borhan

Abstract

The syntheses of haterumalides NA and NC were accomplished via the macrocyclization of a chlorovinylidene chromium carbenoid onto a pendant aldehyde to generate the C8-C9 bond with the desired stereoisomer as the major product. Utilizing the latter chemistry enables access to both C9 hydroxylated (haterumalides NC and ND) and C9 deoxygenated forms (haterumalides NA, NB, and NE; via deoxygenation of the C9-hydroxyl).

References

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Citations

Mar 20, 2013·Chemical Reviews·Adriana LorenteMercedes Álvarez
Mar 12, 2013·Journal of the American Chemical Society·Matthew S McCammantMatthew S Sigman
Aug 29, 2018·Angewandte Chemie·Marc HeinrichAlois Fürstner
Aug 11, 2011·Natural Product Reports·Luiz F Silva, Berit Olofsson
Feb 14, 2019·Natural Product Reports·Kuan Zheng, Ran Hong
Sep 24, 2020·Organic & Biomolecular Chemistry·Rodney A FernandesRamdas S Pathare
Apr 7, 2009·The Journal of Organic Chemistry·Mitsuru UedaHideo Kigoshi
May 26, 2021·The Journal of Organic Chemistry·Emanuele CasaliGiuseppe Zanoni
Jun 26, 2021·Chemical Science·Venugopal Rao ChallaRobert Britton
Oct 12, 2017·Organic Letters·Ichiro HayakawaHideo Kigoshi
Mar 7, 2020·Journal of the American Chemical Society·Marc HeinrichAlois Fürstner
Mar 23, 2019·Organic Letters·André KlüppelMartin Hiersemann

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