Synthetic Study of Marine Macrolide Swinholide A. Stereocontrolled Synthesis of the C11-C32 Segment.

Total Synthesis of Swinholide A

“…In addition, a total of 30 stereogenic centers are present in the carbon backbone of 1 . The important biological properties of swinholide A ( 1 ) and its natural scarcity, coupled with its challenging molecular architecture, made it a prime target for synthesis. − Paterson and his group at Cambridge have already reported the first total synthesis of 1 . In this communication we wish to report an alternative strategy for the total synthesis of 1 that includes a number of conceptually new elements and is flexible enough to allow entry into a variety of designed members of the swinholide class.…”

Synthesis of some novel bioactive 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones via efficient cross-Claisen condensation

“…However there are a few reports on the application of cross-Claisen condensation between different esters or between esters and acid chlorides [20][21][22][23][24]. A nucleophilic reaction of an ester enolate with acid imidazolide has been widely used as a common method for synthesizing b-keto esters [25][26][27][28], but it can be rather expensive to use imidazolide or active ester in industrial setting.…”

Synthetic Studies toward the Total Synthesis of Swinholide. 1. Stereoselective Construction of the C19−C35 Subunit

“…Swinholide A has attracted much interest in the field of synthetic organic chemistry. Paterson 8 and Nicolaou 9 have each completed the synthesis of this large marine macrolide while Nakata has synthesized the monomer preswinholide A and Mulzer 11 has synthesized the C 25 −C 32 tetrapyran subunit.…”