boron and propionaldehyde

boron has been researched along with propionaldehyde* in 1 studies

Other Studies

1 other study(ies) available for boron and propionaldehyde

Article	Year
Development of a third-generation total synthesis of (+)-discodermolide: an expedient Still-Gennari-type fragment coupling utilizing an advanced beta-ketophosphonate. The Journal of organic chemistry, 2005, Jul-08, Volume: 70, Issue:14 [structure: see text] A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8Z)-alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride. Topics: Aldehydes; Alkanes; Antineoplastic Agents; Boron; Carbamates; Ketones; Lactones; Models, Chemical; Organophosphonates; Oxidation-Reduction; Pyrones; Stereoisomerism	2005

Article

Year

Development of a third-generation total synthesis of (+)-discodermolide: an expedient Still-Gennari-type fragment coupling utilizing an advanced beta-ketophosphonate.

The Journal of organic chemistry, 2005, Jul-08, Volume: 70, Issue:14

[structure: see text] A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8Z)-alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride.

Topics: Aldehydes; Alkanes; Antineoplastic Agents; Boron; Carbamates; Ketones; Lactones; Models, Chemical; Organophosphonates; Oxidation-Reduction; Pyrones; Stereoisomerism

2005