282097-88-5Relevant academic research and scientific papers
En route to a plant scale synthesis of the promising antitumor agent 12,13-desoxyepothilone B.
Chappell,Stachel,Lee,Danishefsky
, p. 1633 - 1636 (2000)
[reaction--see text] Efficient and processable syntheses of key building blocks of the antitumor agent 12,13-desoxyepothilone B (dEpoB) by catalytic asymmetric induction are herein described.
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
supporting information; 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.
Insights into long-range structural effects on the stereochemistry of aldol condensations: A practical total synthesis of desoxyepothilone F
Chul Bom Lee,Wu,Zhang,Chappell,Stachel,Chou,Guan,Danishefsky
, p. 5249 - 5259 (2007/10/03)
A processable total synthesis of a potent antitumor agent, desoxyepothilone F (dEpoF, 21-hydroxy-12,13-desoxyepothilone B, 21-hydroxyepothilone D), has been accomplished. The route is highly convergent. The new technology has also been applied to a total
