87764-16-7Relevant academic research and scientific papers
Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol
Watson, Anthony T.,Park, Kwangyong,Wiemer, David F.,Scott, William J.
, p. 5102 - 5106 (2007/10/02)
Racemic arenarol (1) has been synthesized from the known decalin 5β-carbethoxy-1,1-(1,2-ethylenedioxy)-5α,8aβ-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-oxonaphthalene (9) via a short, efficient, and highly stereocontrolled sequence.Key steps in this synthesis are the directed hydrogenation of an unsaturated neopentyl alcohol to provide stereocontrolled formation of the two adjacent tetriary centers and subsequent elaboration of the arenarol skeleton via a nickel-mediated coupling of the corresponding neopentyl iodide.This sequence demonstrates the value of nickel-mediated crosscoupling reactions for carbon-carbon bond formation at neopentyl centers.
Arenarol and Arenarone: Sesquiterpenoids with Rearranged Drimane Skeletons from the Marine Sponge Dysidea arenaria
Schmitz, Francis J.,Lakshmi, Vijai,Powell, Douglas R.,Helm, Dick van der
, p. 241 - 244 (2007/10/02)
Two new sesquiterpenoids, arenarol (3a) and arenarone (4), having identical rearranged drimane skeletons bearing hydroquinol and hydroquinone moieties,respectively, are reported from the Pacific sponge Dysidea arenaria.The structure of arenarol was determined by X-ray analysis of its diacetate which crystallizes in the space group P212121 with unit-cell dimensions (138 K) a: 9.964 (5), b: 6.81 (2), and c: 33.33 (5) . the crystal structure was determined from 2268 data.The final R value is 0.065.Arenarol was chemically correlated with arenarone by silver oxide oxidation.Detailed 400-MHz 1H NMR analysis of arenarol assisted by 2-D J-resolved and 2-D homocorrelation spectroscopy is tabulated.
