22850-55-1Relevant articles and documents
AN EFFICIENT COUPLING REACTION OF ANIONIC PROPARGYL AND ORGANIC HALIDES
Hooz, John,Calzada, Jose G.,McMaster, Denis
, p. 271 - 274 (1985)
The organometallic produced by controlled lithiation of allene functions as an efficient propargylic anion equivalent in coupling reactions with alkyl and allyl halides.
Total Synthesis of (-)-Chromodorolide B by a Computationally-Guided Radical Addition/Cyclization/Fragmentation Cascade
Tao, Daniel J.,Slutskyy, Yuriy,Muuronen, Mikko,Le, Alexander,Kohler, Philipp,Overman, Larry E.
, p. 3091 - 3102 (2018/03/08)
The first total synthesis of a chromodorolide marine diterpenoid is described. The core of the diterpenoid is constructed by a bimolecular radical addition/cyclization/fragmentation cascade that unites two complex fragments and forms two C-C bonds and four contiguous stereogenic centers of (-)-chromodorolide B in a single step. This coupling step is initiated by visible-light photocatalytic fragmentation of a redox-active ester, which can be accomplished in the presence of an iridium or a less-precious electron-rich dicyanobenzene photocatalyst, and employs equimolar amounts of the two addends. Computational studies guided the development of this central step of the synthesis and provide insight into the origin of the observed stereoselectivity.
A convergent approach to coenzyme Q
Lipshutz, Bruce H.,Bulow, Gerd,Fernandez-Lazaro, Fernando,Kim, Sung-Kyu,Lowe, Richard,Mollard, Paul,Stevens, Kirk L.
, p. 11664 - 11673 (2007/10/03)
Syntheses of coenzyme Q3-8 are described, as well as related systems such as plastoquinone-5. Preparation of the higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.
