1392284-90-0Relevant articles and documents
Modular total synthesis of rhizopodin: A highly potent G-actin dimerizing macrolide
Kretschmer, Manuel,Dieckmann, Michael,Li, Pengfei,Rudolph, Sven,Herkommer, Daniel,Troendlin, Johannes,Menche, Dirk
, p. 15993 - 16018 (2014/04/03)
A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29steps by employing a concise strategy that exploits the molecule′s C2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site-directed sequential cross-coupling strategy and the bidirectional attachment of the side chains by means of Horner-Wadsworth-Emmons (HWE) coupling reactions. During the course of this endeavor, scalable routes for synthesis of three main building blocks of similar complexity were developed that allowed for their stereocontrolled construction. This modular route will be amenable to the development of syntheses of other analogues of rhizopodin.
Studies on C18-C20 aldol couplings of rhizopodin
Dieckmann, Michael,Rudolph, Sven,Lang, Carolin,Ahlbrecht, Wiebke,Menche, Dirk
, p. 2305 - 2315 (2013/09/02)
The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection. Georg Thieme Verlag Stuttgart. New York.