1258870-40-4Relevant academic research and scientific papers
A gram-scale batch and flow total synthesis of perhydrohistrionicotoxin
Brasholz, Malte,MacDonald, James M.,Saubern, Simon,Ryan, John H.,Holmes, Andrew B.
experimental part, p. 11471 - 11480 (2010/11/24)
The total synthesis of the spi- ropiperidine alkaloid (-)-perhydrohis- trionicotoxin (perhydro-HTX) 2 has been accomplished on a gram scale by employing both conventional batch chemistry as well as microreactor techniques. )-6-Pentyltetrahydro- pyran-2-one 8 underwent nucleophilic ring opening to afford the alcohol 10, which was elaborated to the nitrone 13. Protection of the nitrone as the 1,3- adduct of styrene and side-chain extension to the unsaturated nitrile afforded a precursor 17, which underwent dipolar cycloreversion and 1,3-dipolar cycloaddition to give the core spirocyclic precursor 18 that was converted into perhydro-HTX 2. The principal steps to the spirocycle 18 have successfully been transferred into flow mode by using different types of microreactors and in a telescoped fashion, allowing for a more rapid access to the histrioni- cotoxins and their analogues by continuous processing.
