Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin

Journal of the American Chemical Society
Xiayun Cheng, Glenn C Micalizio

Abstract

An asymmetric approach to the synthesis of neurotrophic seco-prezizaane sesquiterpenes is described that is based on the strategic application of a hydroxyl-directed metallacycle-mediated [2 + 2 + 2] annulation and an intramolecular radical cyclization cascade. Targets prepared are among the most potent members of the natural product class and include (1R,10S)-2-oxo-3,4-dehydroneomajucin, (2S)-hydroxy-3,4-dehydroneomajucin, and (-)-jiadifenin. In addition to representing the first application of the alkoxide-directed metallacycle-mediated hydrindane-forming annulation reaction in natural product synthesis and the first total synthesis of (2S)-hydroxy-3,4-dehydroneomajucin, these pursuits have resulted in the elucidation of a complex radical cascade process for installation of the C5 quaternary center common to the natural product class.

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Citations

Oct 16, 2016·The Journal of Organic Chemistry·José GomesKarl Gademann
Dec 15, 2016·Journal of the American Chemical Society·Kevin HungThomas J Maimone
Jun 24, 2017·Journal of the American Chemical Society·Masaki OhtawaRyan A Shenvi
Aug 28, 2020·Chemical Society Reviews·Manfred Manßen, Laurel L Schafer
Jun 28, 2017·Israel Journal of Chemistry·Glenn C Micalizio, Haruki Mizoguchi
Jul 10, 2020·Journal of Natural Medicines·Yoshiyasu FukuyamaKenichi Harada
Apr 17, 2019·Nature Reviews. Chemistry·Evan P BeaumierIan A Tonks
Feb 13, 2020·Journal of the American Chemical Society·Bin Cai, James S Panek
Feb 3, 2018·Journal of the American Chemical Society·Jin-Xin ZhaoJian-Min Yue
Nov 18, 2017·Journal of the American Chemical Society·Matthew L CondakesThomas J Maimone
Dec 12, 2018·The Journal of Organic Chemistry·Matthew L CondakesThomas J Maimone
Mar 9, 2018·Chemical Reviews·Lei LiYanxing Jia
Aug 29, 2017·Journal of the American Chemical Society·Matthew J KierGlenn C Micalizio
Jan 31, 2019·Journal of the American Chemical Society·Kevin HungThomas J Maimone
Sep 18, 2021·ACS Medicinal Chemistry Letters·Lauren E MarkhamGlenn C Micalizio

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