501084-23-7Relevant academic research and scientific papers
Diarylprolinol-Mediated Asymmetric Direct Cross-Aldol Reaction of α,β-Unsaturated Aldehyde as an Electrophilic Aldehyde
Hayashi, Yujiro,Nagai, Kaito,Umemiya, Shigenobu
, p. 4146 - 4149 (2019)
The diarylprolinol-mediated asymmetric direct cross-aldol reaction of α,β-unsaturated aldehyde as an electrophilic aldehyde was developed. The reaction becomes accelerated by an acid when a carbonyl group is introduced at the γ-position of the α,β-unsatur
The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments
Paterson, Ian,Anderson, Edward A.,Dalby, Stephen M.,Lim, Jong Ho,Maltas, Philip,Loiseleur, Olivier,Genovino, Julien,Moessner, Christian
experimental part, p. 5861 - 5872 (2012/08/28)
Due to a combination of their promising anticancer properties, limited supply from the marine sponge source and their unprecedented molecular architecture, spirastrellolides represent attractive and challenging synthetic targets. A modular strategy for the synthesis of spirastrellolide A methyl ester, which allowed for the initial stereochemical uncertainties in the assigned structure was adopted, based on the envisaged sequential coupling of a series of suitably functionalised fragments; in this first paper, full details of the synthesis of these fragments are described. The pivotal C26-C40 DEF bis-spiroacetal was assembled by a double Sharpless asymmetric dihydroxylation/acetalisation cascade process on a linear diene intermediate, configuring the C31 and C35 acetal centres under suitably mild acidic conditions. A C1-C16 alkyne fragment was constructed by application of an oxy-Michael reaction to introduce the A-ring tetrahydropyran, a Sakurai allylation to install the C9 hydroxyl, and a 1,4-syn boron aldol/directed reduction sequence to establish the C11 and C13 stereocentres. Two different coupling strategies were investigated to elaborate the C26-C40 DEF fragment, involving either a C17-C25 sulfone or a C17-C24 vinyl iodide, each of which was prepared using an Evans glycolate aldol reaction. The remaining C43-C47 vinyl stannane fragment required for introduction of the unsaturated side chain was prepared from (R)-malic acid.
Total synthesis of spirastrellolide A methyl ester - Part 1: Synthesis of an advanced C17-C40 bis-spiroacetal subunit
Paterson, Ian,Anderson, Edward A.,Dalby, Stephen M.,Lim, Jong Ho,Genovino, Julien,Maltas, Philip,Moessner, Christian
, p. 3016 - 3020 (2008/12/23)
Out of the blue: The marine macrolide spirastrellolide A is a potent and selective inhibitor of protein phosphatase 2A and a lead for anticancer therapies. A flexible and modular synthetic strategy has been developed with two routes for the construction o
Synthesis and conformational analysis of meso-ter(1,3-dioxan-4-yls)
Hoffmann, Reinhard W.,Mas, Gemma,Brandl, Trixi
, p. 3455 - 3464 (2007/10/03)
A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure ass
