934672-43-2Relevant academic research and scientific papers
A reductive coupling strategy towards ripostatin A
Schleicher, Kristin D.,Jamison, Timothy F.
, p. 1533 - 1550 (2013/10/22)
Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment corresponding to C1-C9 has been synthesized in high yield and demonstrated to be a competent substrate for the nickel(0)-catalyzed coupling with a model epoxide. Several synthetic approaches toward the C10-C26 epoxide have been pursued. The C13 stereocenter can be set by allylation and reductive decyanation of a cyanohydrin acetonide. A mild, fluoride-promoted decarboxylation enables construction of the C15-C16 bond by an aldol reaction. The product of this transformation is of the correct oxidation state and potentially three steps removed from the targeted epoxide fragment.
Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: A cationic cascade cyclization
Li, Bin,Zhao, Yu-Jun,Lai, Yin-Chang,Loh, Teck-Peng
supporting information; experimental part, p. 8041 - 8045 (2012/09/05)
High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used. Copyright
Access to skipped polyene macrolides through ring-closing metathesis: Total synthesis of the RNA polymerase inhibitor ripostatin B
Winter, Philipp,Hiller, Wolf,Christmann, Mathias
, p. 3396 - 3400 (2012/06/16)
Rip-Roaring! A convergent total synthesis of antibiotic ripostatin B was developed. A key step in the synthesis is a metathesis reaction allowing for a ring closure to the labile doubly skipped triene macrolide. Copyright
Transforming terpene feedstock into polyketide architecture
Winter, Philipp,Vaxelaire, Carine,Heinz, Christoph,Christmann, Mathias
, p. 394 - 396 (2011/03/17)
The Cu-catalyzed synthesis of skipped 1,4-dienes from allylic acetates and vinyl-Grignard reagents is key to bidirectional modifications of acyclic terpene acetates. As a result, trisubstituted double bond containing subunits can be readily transferred into complex polyketides from inexpensive bulk terpenes.
Synthesis of the C1-C5 and C6-C24 fragments of the RNA polymerase inhibitors ripostatin A and B
Kujat, Christof,Bock, Martin,Kirschning, Andreas
, p. 419 - 422 (2007/10/03)
The enantioselective synthesis of the C1-C5 and C6-C24 fragments of the ripostatins utilize a Negishi coupling, two Nagao acetate aldol reactions followed by a Denmark vinylogous aldol reaction and Stille couplings as key C-C bond forming steps. Georg Thi
