364597-23-9Relevant academic research and scientific papers
Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: A facile and stereoselective approach
Bujaranipalli, Sheshurao,Das, Saibal
, p. 3747 - 3749 (2015/06/08)
A concise and facile synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin has been demonstrated in 12 steps starting from methylacetoacetate and (±)propylene oxide. The key reactions involved are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu, and ring closing metathesis reaction for the construction of macrolactone with two chiral substitutions on it.
Towards the total synthesis of marineosin A: Construction of the macrocyclic pyrrole and an advanced, functionalized spiroaminal model
Aldrich, Leslie N.,Berry, Cynthia B.,Bates, Brittney S.,Konkol, Leah C.,So, Miranda,Lindsley, Craig W.
supporting information, p. 4215 - 4218 (2013/07/26)
Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1 % overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is subjected to Paal-Knorr pyrrole synthesis and ring-closing metathesis to afford the macrocycle. A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system through an acid-mediated hydroxy oxo amide cyclization strategy. Copyright
A short and facile stereoselective total synthesis of cryptocarya diacetate
Yadav, Jhillu S.,Reddy, P. Murali Krishna,Gupta, Manoj K.,Reddy, Basi V. Subba
, p. 1583 - 1587 (2013/10/22)
A short, simple, and efficient stereoselective total synthesis of cryptocarya diacetate using benzylidene acetal as a key intermediate is described. The synthesis proceeded with overall yield of 10 % starting from commercially available (S)-ethyl lactate.
A short enantioselective synthesis of the topoisomerase II inhibitor (+)-eleutherin
Gibson, Jennifer S.,Andrey, Olivier,Brimble, Margaret A.
, p. 2611 - 2613 (2008/02/13)
A Hauser-Kraus annulation was used as a key step for the concise enantioselective synthesis of the topoisomerase II inhibitor (+)-eleutherin. Georg Thieme Verlag Stuttgart.
A total synthesis of xestodecalactone A and proof of its absolute stereochemistry: Interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes
Yoshino, Toshiharu,Ng, Fay,Danishefsky, Samuel J.
, p. 14185 - 14191 (2008/02/10)
A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered.
Solution- and solid-phase synthesis of radicicol (monorden) and pochonin C
Barluenga, Sofia,Moulin, Emilie,Lopez, Pilar,Winssinger, Nicolas
, p. 4935 - 4952 (2007/10/03)
A modular synthesis for pochonin C and radicicol is reported. The two natural products were prepared in seven and eight steps, respectively, from three readily available fragments. Alternative syntheses of these compounds were achieved using a combination of polymer-bound reagents and solid phase reactions. The conformation of the two natural products was studied and compared by using 2D NMR spectroscopy.
Modular asymmetric synthesis of pochonin C
Barluenga, Sofia,Lopez, Pilar,Moulin, Emilie,Winssinger, Nicolas
, p. 3467 - 3470 (2007/10/03)
Back to its origins: Pochonin C was synthesized in 11 steps from the four fragments shown in the scheme. This asymmetric synthesis and the conversion of pochonin C into radicicol defines the configuration at the center bearing the chlorine atom as S. lpc
Concise asymmetric syntheses of radicicol and monocillin I
Garbaccio,Stachel,Baeschlin,Danishefsky
, p. 10903 - 10908 (2007/10/03)
Radicicol (1) exhibits potent anticancer properties in vitro, which are likely to be mediated through its high affinity (20 nM) for the molecular chaperone Hsp90. Recently, we reported the results of a synthetic program targeting radicicol (1) and monocil
