130248-05-4Relevant academic research and scientific papers
Diastereoselective cyclisation of N-alkenylideneamines into 3,4-dihydro-2H-pyrrol-1-ium halides
Schley, Daniela,Liebscher, Juergen
, p. 2945 - 2957 (2008/02/09)
A number of new chiral 2-(α-bromoalkyl)pyrrolinium salts and 2-(α-selenoalkyl)pyrrolidines were synthesized by the halocyclisation and selenocyclisation, respectively, of N-(alkenylidene)alkylamines and subsequent reduction. These cyclisations were implem
1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A
Pérez-Balado, Carlos,Markó, István E.
, p. 2331 - 2349 (2007/10/03)
syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes with DIBAL-H followed by Al/I exchange with I2 afforded exclusively (E)-1-iodo-1-selenoalkenes in good yields. 1-Iodo-1-selenopropene 10 proved to be a convenient 1,1 dianion equivalent, leading to the stereodivergent synthesis of allylsilanes (Z)-6 and (E)-6. Adduct 3, an intermediate in the synthesis of the tetrahydropyran subunit of polycavernoside A, was efficiently synthesised from allylsilane (Z)-6 and aldehyde 7 via an intramolecular Sakurai cyclisation.
Stereoselective synthesis of (E)-1-iodo-1-selenoalkenes via hydroalumination-iodination of 1-alkynyl selenides
Pérez-Balado, Carlos,Lucaccioni, Fabio,Markó, István E.
, p. 4883 - 4886 (2007/10/03)
syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes 22 with DIBAL-H, followed by Al/I exchange with I2, afforded selectively the corresponding (E)-1-iodo-1-selenoalkenes in good yields. The sterically hindered 2,4,6-triisopropylphenyl group proved to be mandatory and prevented the formation of undesired by-products.
Leucascandrolide A: Synthesis and Related Studies
Fettes, Alec,Carreira, Erick M.
, p. 9274 - 9283 (2007/10/03)
The total synthesis of the biologically active marine natural product leucascandrolide A is reported. A convergent strategy is employed, allowing for the rapid assembly of the macrolide moiety. Key steps of our approach include the diastereoselective addi
