472979-36-5Relevant academic research and scientific papers
Enantioselective synthesis of the C(1)-C(11) fragment of tedanolide C
Geist, Julie G.,Barth, Roland,Roush, William R.
supporting information, p. 58 - 61 (2013/03/28)
A convergent synthesis of the protected C(1)-C(11) fragment 6 of the targeted enantiomer of tedanolide C is described. The key step of the synthesis is the Felkin-Ahn addition of vinyl iodide 7 to aldehyde 8 that proceeds in 80% yield with 4:1 diastereose
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.
Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin
Kretschmer, Manuel,Menche, Dirk
supporting information; experimental part, p. 382 - 385 (2012/02/16)
A convergent synthesis of the central C8-C22 core of the potent macrolide antibiotic rhizopodin is reported. Notable features of the stereocontrolled approach include an asymmetric reverse prenylation of an alcohol using a method of Krische, a thiazolium catalyzed transformation of an epoxyaldehyde as described by Bode, and a late-stage oxazole formation from advanced intermediates. This route demonstrates the applicability of these methodologies in complex natural product synthesis.
Studies towards the synthesis of epothilone A via organoboranes
Ramachandran, P. Veeraraghavan,Chandra, J. Subash,Prabhudas, Bodhuri,Pratihar, Debarshi,Reddy, M. Venkat Ram
, p. 3812 - 3824 (2007/10/03)
Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-γ,γ-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction wit
Preparative-scale synthesis of both antipodes of B-γ,γ- dimethylallyldiisopinocampheylborane: Application for the synthesis of C 1-C6 subunit of epothilone
Ramachandran, P. Veeraraghavan,Prabhudas, Bodhuri,Chandra, J. Subash,Reddy, M. Venkat Ram,Brown, Herbert C.
, p. 1011 - 1013 (2007/10/03)
A preparative-scale synthesis of B-γ,γ- dimethylallyldiisopinocampheylborane starting from prenyl alcohol has been described. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-dimethylhomoallylic alcohols in high enantiose
Toward the total synthesis of disorazole A(1) and C(1): asymmetric synthesis of a masked southern segment.
Hartung, Ingo V,Niess, Barbara,Haustedt, Lars Ole,Hoffmann, H Martin R
, p. 3239 - 3242 (2007/10/03)
[reaction: see text] A highly convergent asymmetric synthesis of the masked southern segment of the antimitotic agent disorazole A(1) involves a Sonogashira coupling between a C1'-C10' enyne and a suitably protected C11'-C19' vinyl iodide. The central E,Z,Z-triene moiety is masked as a more stable ynediene.
