102808-49-1Relevant academic research and scientific papers
Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents
Packard, Emma,Pascoe, David D.,Maddaluno, Jacques,Goncalves, Theo P.,Harrowven, David C.
supporting information, p. 13076 - 13079 (2014/01/06)
Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.
Total Syntheses of Furaquinocin A, B, and E
Trost, Barry M.,Thiel, Oliver R.,Tsui, Hon-Chung
, p. 13155 - 13164 (2007/10/03)
A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain via Horner-Wadsworth-Emmons reaction and assembly of the naphthoquinone with squaric acid based methodology leads to furaquinocin E. The use of differentially substituted squaric acid derivatives allows the synthesis of three analogues of furaquinocin E. The additional stereocenters in furaquinocin A and B can be introduced with a diastereoselective Sakurai allylation. The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B.
A General, Regiospecific Synthesis of Highly Substituted Quinones
Liebeskind, Lanny S.,Iyer, Suresh,Jewell, Charles F.
, p. 3065 - 3067 (2007/10/02)
A general route to a wide variety of substituted quinones (furyl, indolo, pyrrolo, quinolino, naphtho, and anthra) has been developed via the thermolysis (160 deg C, xylene) and subsequent oxidation (air or Ce4+) of 4-hydroxy-4-substituted-cyclobutenones (eq. 1) and 2-hydroxy-2-substituted-benzocyclobutenones which were formed by the regioselective addition of an appropriate aryl or heteroaryl (etc.) lithium reagent to the correspnding cyclobutenedione.
