529494-98-2Relevant academic research and scientific papers
A fully stereocontrolled total synthesis of (+)-leucascandrolide A
Paterson, Ian,Tudge, Matthew
, p. 6833 - 6849 (2003)
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.
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.
