87764-13-4Relevant academic research and scientific papers
An efficient synthesis of (+)-aureol via boron trifluoride etherate-promoted rearrangement of (+)-arenarol
Nakamura, Masahiko,Suzuki, Akiyuki,Nakatani, Mari,Fuchikami, Takamasa,Inoue, Munenori,Katoh, Tadashi
, p. 6929 - 6932 (2007/10/03)
A novel marine natural product, (+)-aureol (1), was efficiently synthesized starting from the cis-fused decalin derivative 4. The synthetic method features boron trifluoride etherate-promoted rearrangement/cyclization reaction of (+)-arenarol (2) to form
Studies toward the synthesis of popolohuanone E: Synthesis of natural (+)-arenarol related to the proposed biogenetic precursor of popolohuanone E
Kawano, Hideki,Itoh, Masanori,Katoh, Tadashi,Terashima, Shiro
, p. 7769 - 7772 (2007/10/03)
The cis-fused decalin segment 6 required for the total synthesis of popolohuanone E (1) was efficiently synthesized starting from the enantiomerically pure (-)-Wieland-Miescher ketone derivative 9; the method features ortho ester Claisen rearrangement of
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.
