862475-25-0Relevant academic research and scientific papers
The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The CD-spiroacetal segment
Paterson, Ian,Coster, Mark J.,Chen, David Y.-K.,Gibson, Karl R.,Wallace, Debra J.
, p. 2410 - 2419 (2007/10/03)
Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.
ACYCLIC STEREOSELECTION. 20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL α- AND β-ALKOXY ALDEHYDES.
Kiyooka, Syun-ichi,Heathcock, Clayton H.
, p. 4765 - 4768 (2007/10/02)
Stannic chloride is an effective catalyst for the reaction of allylsilanes with chiral α- and β-alkoxy aldehydes.In the case of α-alkoxy aldehyde 1, the diastereofacial preference is outstanding (>35:1).With β-alkoxy aldehydes 5 and 6, selectivity lower, but still quite acceptable (7-12:1).
