56410-49-2Relevant academic research and scientific papers
NATURAL PRODUCT SYNTHESIS VIA THE POLYBROMO KETONE-IRON CARBONYL REACTION
Noyori, R.,Hayakawa, Y.
, p. 5879 - 5886 (2007/10/02)
Application of the polybromo ketone-iron carbonyl reaction to natural product synthesis is summarized.The general synthesis of tropane alkaloids has been achieved via the reductive cyclocoupling of sym-tetrabromoacetone with N-methoxycarbonylpyrrole as the key step.Ready availability of 8-oxabicyclooct-6-en-3-one from the tetrabromoacetone and furan has opened a new, efficient entry to natural C-nucleosides including pseudouridine, pseudocytidine, and showdomycin.The artificial analogues such as 2-thiopseudouridine, 6-azapseudouridine, pseudoisocytidine, etc., are also obtainable.The oxabicyclic ketones bearing an isopropyl substituent at the appropriate position serve as intermediates for the synthesis of naturally occurring troponoids, nezukone, α-thujaplicin, and hinokitiol (β-thujaplicin).Carbocamphenilone and camphenic acid have been prepared through the reaction of 1,1,3-tribromo-3-methylbutan-2-one and cyclopentadiene.The cyclocondensation of α,α'-dibromo ketone and a styrene derivative leads to the single-step synthesis of α-cuparenone. 1,3-Dibromo-3,7-dimethyloct-6-en-2-one derived from nerol (or geraniol) undergoes the biogenetic-type double cyclization.The iron carbonyl-assisted intramolecular cyclocoupling gives camphor accompanied by other monoterpenic ketones.A mixture of campherenone and epicampherenone has been obtained from related dibromo ketone prepared from farnesols.The hetero reaction by use of dibromo ketones and N,N-dimethylcarboxamides, forming 3 (2H)-furanones, is employable for the preparation of muscarine alkaloid derivatives.
