952103-58-1Relevant academic research and scientific papers
Synthesis of the C1-C13 tetraenoate subunit of the chivosazoles
Paterson, Ian,Kan, S. B. Jennifer,Gibson, Lisa J.
supporting information; experimental part, p. 3724 - 3727 (2010/11/04)
Using a combination of asymmetric vinylogous Mukaiyama aldol and Stille cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated
Total synthesis of the originally proposed and revised structures of palmerolide A and isomers thereof
Nicolaou,Sun, Ya-Ping,Guduru, Ramakrishna,Banerji, Biswadip,Chen, David Y.-K.
, p. 3633 - 3644 (2008/09/20)
Palmerolide A is a recently disclosed marine natural product possessing striking biological properties, including potent and selective activity against the melanoma cancer cell line UACC-62. The total syntheses of five palmerolide A stereoisomers, including the originally proposed (1) and the revised [ent-(19-epi-20-epi-1)] structures, have been accomplished. The highly convergent and flexible strategy developed for these syntheses involved the construction of key building blocks 2, 19-epi-2, 20-epi-2, ent-2, 3, ent-3, 4, and enf-4, and their assembly and elaboration to the target compounds. For the union of the building blocks, the Stille coupling reaction, Yamaguchi esterification, Horner-Wadsworth-Emmons olefination, and ring-closing metathesis reaction were employed, the latter being crucial for the stereoselective formation of the macrocycle of the palmerolide structure. The Horner-Wadsworth-Emmons olefination and the Yamaguchi lactonization were also investigated and found successful as a means to construct the palmerolide macrocycle. The syntheses were completed by attachment of the enamide moiety through a copper-catalyzed coupling process.
Total synthesis of the originally proposed and revised structures of palmerolide A
Nicolaou,Guduru, Ramakrishna,Sun, Ya-Ping,Banerji, Biswadip,Chen, David Y.-K.
, p. 5896 - 5900 (2008/09/16)
(Chemical Equation Presented) In the palm of your hand: Total syntheses of the originally proposed and revised structures of the marine antitumor agent palmerolide A (see picture, originally proposed structure had opposite configurations at the positions indicated in red) were accomplished through a modular strategy that features a ring-closing metathesis to stereoselectively form the C8=C9 bond and concurrently form the macrocycle.
