529494-85-7Relevant academic research and scientific papers
An organocascade kinetic resolution
McGarraugh, Patrick G.,Brenner-Moyer, Stacey E.
, p. 6460 - 6463 (2012/02/14)
Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and, notably, cascade products with absolute and relative configurations normally not observed using this diphenyl prolinol silyl ether. This resolution thus provides new insight into asymmetric induction in reactions employing this catalyst.
Enantioselective total synthesis of (-)-dactylolide
Louis, Ignace,Hungerford, Natasha L.,Humphries, Edward J.,McLeod, Malcolm D.
, p. 1117 - 1120 (2007/10/03)
The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence
Stereocontrolled total synthesis of (+)-leucascandrolide A
Paterson, Ian,Tudge, Matthew
, p. 343 - 347 (2007/10/03)
Apparently no longer available from its natural source is the potent cytotoxic and antifungal agent leucascandrolide A (1), which was initially isolated from a New Caledonian calcareous sponge. A highly stereocontrolled total synthesis of this structurally unique macrolide commences with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the tetrahydropyran ring. An efficient endgame relies on two Mitsunobu reactions, the first to generate the 18-membered macrolactone and the second to attach the oxazole-bearing side chain.
A fully stereocontrolled total synthesis of (+)-leucascandrolide A
Paterson, Ian,Tudge, Matthew
, p. 6833 - 6849 (2007/10/03)
A highly stereocontrolled total synthesis of leucascandrolide A, a cytotoxic 18-membered macrolide from the calcareous sponge Leucascandra caveolata, starts out with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the 2,6-cis-tetrahydropyran ring. All the remaining oxygenated stereocentres are introduced with high selectivity by relying on substrate-based control. An efficient endgame depends on two Mitsunobu reactions, the first to close the macrolactone with inversion at C17 and the second to attach the oxazole-containing side chain at C5, followed by Lindlar hydrogenation of the two alkynes to provide (+)-leucascandrolide A.
