591770-18-2Relevant articles and documents
Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers
Shin, Youseung,Fournier, Jean-Hugues,Brückner, Arndt,Madiraju, Charitha,Balachandran, Raghavan,Raccor, Brianne S.,Edler, Michael C.,Hamel, Ernest,Sikorski, Rachel?P.,Vogt, Andreas,Day, Billy W.,Curran, Dennis P.
, p. 8537 - 8562 (2008/02/09)
Total syntheses of (-)-dictyostatin, 6,16-bis-epi-dictyostatin, 6,14,19-tris-epi-dictyostatin, and a number of other isomers and analogs are reported. Three main fragments-top, middle, and bottom-were first assembled and then joined by olefination or anio
ANALOGS OF DICTYOSTATIN, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF
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, (2008/06/13)
Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and i
Facile generation of alkenes and dienes from tosylates
Phukan, Prodeep,Bauer, Matthias,Maier, Martin E.
, p. 1324 - 1328 (2007/10/03)
Several aldol products resulting from Evans aldol reactions were converted to primary alcohols. After conversion to the corresponding tosylates, heating with NaI and DBU in dimethoxyethane (glyme) effected clean elimination to the terminal olefin. This simple one-pot procedure was applied to other tosylates and a tosylate derived from a homoallylic alcohol. The latter gave rise to a diene.
Flexible routes to the 5-hydroxy acid fragment of the cryptophycins
Phukan, Prodeep,Sasmal, Sanjita,Maier, Martin E.
, p. 1733 - 1740 (2007/10/03)
Two solutions to establishing the anti stereochemistry of the vicinal stereocenters in the 5-hydroxy acid subunit of cryptophycin, based on initial Evans syn aldol reactions between an N-(propionyl)oxazolidinone 4 and a C3 aldehyde, were developed. In the first route, the secondary hydroxy group was inverted by use of Mitsunobu reaction conditions, whereas the second route features an inversion of the methyl-bearing stereocenter, achieved by reductive removal of the chiral auxiliary, elimination to afford the terminal alkene, and anti-selective hydroboration. The aryl part can be attached either by Wittig-Horner olefination or by a modified Julia coupling. Both routes provide the hydroxy acid 16 in a very efficient manner. The substrate for the hydroboration, alkene 22, could also be obtained from (S)-malic acid. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.