Total synthesis of (12R)- and (12S)-12-hydroxymonocerins: stereoselective oxylactonization using a chiral hypervalent iodine(iii) species

RSC Advances ◽  
2013 ◽  
Vol 3 (39) ◽  
pp. 17717 ◽  
Author(s):  
Morifumi Fujita ◽  
Kazuhiro Mori ◽  
Mio Shimogaki ◽  
Takashi Sugimura
Keyword(s):  
Total Synthesis ◽  
Hypervalent Iodine

Total synthesis of discorhabdin C: a general aza spiro dienone formation from O-silylated phenol derivatives using a hypervalent iodine reagent

1992 ◽  
Vol 114 (6) ◽  
pp. 2175-2180 ◽  
Author(s):  
Yasuyuki Kita ◽  
Hirofumi Tohma ◽  
Masanao Inagaki ◽  
Kenji Hatanaka ◽  
Takayuki Yakura
Keyword(s):  
Total Synthesis ◽  
Hypervalent Iodine ◽  
Phenol Derivatives

scholarly journals Hypervalent Iodine-Mediated Vicinal syn Diazidation: Application to the Total Synthesis of (.+-.)-Dibromophakellstatin.

ChemInform ◽  
2005 ◽  
Vol 36 (6) ◽  
Author(s):  
Raymond Chung ◽  
Eunsun Yu ◽  
Christopher D. Incarvito ◽  
David J. Austin
Keyword(s):  
Total Synthesis ◽  
Hypervalent Iodine

scholarly journals Total synthesis of natural products using hypervalent iodine reagents

2015 ◽  
Vol 2 ◽  
Author(s):  
Gaëtan Maertens ◽  
Chloé L'Homme ◽  
Sylvain Canesi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Hypervalent Iodine

scholarly journals Unprecedented and Scalable Copper (I)-Catalyzed Oxidation of the Csp2-H bond on 2-phenyl-naphthalene-1,3-diol with Atmospheric Oxygen: synthesis of 2-Hydroxy-3-phenyl-1,4-naphthoquinone via direct Csp2-O bond formation

2017 ◽  
Vol 27 (5) ◽  
pp. 62-68 ◽  
Author(s):  
Sheila Teresita Guardado-Cruz ◽  
Rafael Ortiz-Alvarado ◽  
Claudia De León ◽  
César Rogelio Solorio-Alvarado
Keyword(s):  
Total Synthesis ◽  
Atmospheric Oxygen ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Direct Oxidation ◽  
Oxidative Dimerization ◽  
Reaction Conditions ◽  
Oxidation Processes ◽  
Dimerization Product ◽  
Catalyzed Oxidation

The Csp2-O bond formation via direct oxidation of the Csp2-H bond on electron-rich compounds such as naphthols, is a process that generally requires drastic reaction conditions like high temperature or pressure. Addition of strong oxidants as H2O2, hypervalent iodine reagents (λ3 o λ5), expensive transition metals or rare earth elements, such as Mo, Ru Pt or Ce, is usually necessary. As part of this study on oxidative dimerization of phenols towards the total synthesis of ningalin D, 1,3-naphthalenediol was explored as starting material using stoichiometric amounts of Cu(I) and atmospheric molecular oxygen. A novel two-step sequence reaction for the formation of a 1,4-naphthoquinone was found instead of a dimerization product. The synthesis of this compound involves two consecutive oxidation processes. 

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