Total synthesis of lamellarins D, L, and N

Fujikawa, Naotaka; Ohta, Takeshi; Yamaguchi, Tomohiro; Fukuda, Tsutomu; Ishibashi, Fumito; Iwao, Masatomo

doi:10.1016/j.tet.2005.10.014

Cited by 99 publications

(66 citation statements)

References 39 publications

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“…Iwao et al also reported the synthesis of 36, 37, and 40 in 19%, 18%, and 16% yields over 11, 12, and 12 steps, respectively. They started from isopropyl-protected isovanillin and applied a nitroaldol condensation, a N-dialkylation and Hinsberg pyrrole cyclization reactions (Scheme 8b) [110].…”

Section: Lamellarins and Derivativesmentioning

confidence: 99%

Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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Multidrug resistance (MDR) to anticancer drugs is a serious health problem that in many cases leads to cancer treatment failure. The ATP binding cassette (ABC) transporter P-glycoprotein (P-gp), which leads to premature efflux of drugs from cancer cells, is often responsible for MDR. On the other hand, a strategy to search for modulators from natural products to overcome MDR had been in place during the last decades. However, Nature limits the amount of some natural products, which has led to the development of synthetic strategies to increase their availability. This review summarizes the research findings on marine natural products and derivatives, mainly alkaloids, polyoxygenated sterols, polyketides, terpenoids, diketopiperazines, and peptides, with P-gp inhibitory activity highlighting the established structure-activity relationships. The synthetic pathways for the total synthesis of the most promising members and analogs are also presented. It is expected that the data gathered during the last decades concerning their synthesis and MDR-inhibiting activities will help medicinal chemists develop potential drug candidates using marine natural products as models which can deliver new ABC transporter inhibitor scaffolds.

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Section: Lamellarins and Derivativesmentioning

confidence: 99%

Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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“…We chose these two highly polar solvents as it is known that polar solvents drive the bromination reaction through the stabilization of bromocyclohexadienone-type intermediates. [17] DMF [18] as well as MeCN [15] have been described previously as good solvents for nuclear bromination reactions of aromatic systems with NBS. However, the bromination of a polyphenol with NBS in THF has only been reported once, [19] and has only rarely been used for the bromination of monosubstituted methoxy-or benzyloxyanilines.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Monobromination of Free and Protected Phenols

2007

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A comparative study of the advantages of using THF compared with DMF in regioselective monobromination reactions of highly activated polyphenols, their ethers, and their tert-butyl carbonate derivatives under mild conditions is described. Bromination with the common reagent N-bromosuccinimide in polar solvents provided an easy and fast approach to aromatic electrophilic substitution at the most elec-

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“…[56][57][58] For example, the total synthesis of lamellarins L (26) and N (105) is shown in Scheme 16. Intermediate (110) was prepared by convergent assembly of bistriflate (106) and arylboronic acids (107) and (108) in a similar manner as described above.…”

Section: -2-2 Synthesis By Iwao (I)mentioning

confidence: 99%