Total Synthesis of Biselide E, a Marine Polyketide

Hayakawa, Ichiro; Suzuki, Kazuaki; Okamura, Masami; Funakubo, Shota; Onozaki, Yuto; Kawamura, Dai; Ohyoshi, Takayuki; Kigoshi, Hideo

doi:10.1021/acs.orglett.7b03009

Cited by 6 publications

(3 citation statements)

References 23 publications

(11 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further 27 steps were required to obtain natural biselide A (Scheme 8). Likewise, Kigoshi has also described the total synthesis of biselide E, from common advanced intermediate 52 [46].…”

Section: Haterumalides and Biselidesmentioning

confidence: 99%

The Tetrahydrofuran Motif in Polyketide Marine Drugs

et al. 2022

View full text Add to dashboard Cite

Oxygen heterocycles are units that are abundant in a great number of marine natural products. Among them, marine polyketides containing tetrahydrofuran rings have attracted great attention within the scientific community due to their challenging structures and promising biological activities. An overview of the most important marine tetrahydrofuran polyketides, with a focused discussion on their isolation, structure determination, approaches to their total synthesis, and biological studies is provided.

show abstract

“…Further 27 steps were required to obtain natural biselide A (Scheme 8). Likewise, Kigoshi has also described the total synthesis of biselide E, from common advanced intermediate 52 [46].…”

Section: Haterumalides and Biselidesmentioning

confidence: 99%

The Tetrahydrofuran Motif in Polyketide Marine Drugs

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Introduction of the chloroacetyl groups at all hydroxy groups in the triol and the removal of the 2,4-DMPM esters gave the desired carboxylic acid, which underwent an iPr 2 NEt-caused β-elimination of the chloroacetoxy group to afford the desired sixmembered α,β,γ,δ-doubly unsaturated lactone. The two chloroacetyl groups were removed by the use of Zn(OAc) 2 in MeOH (Hayakawa et al, 2017b).…”

Section: Fig 28mentioning

confidence: 99%

Ascidian halogen-containing secondary metabolites from the family didemnidae

Djordjevic

Radulović

2019

Facta Univ Phys Chem Technol

View full text Add to dashboard Cite

This review summarizes current knowledge concerning the isolation, structural elucidation, biological/pharmacological activities, and total synthesis of halogen-containing secondary metabolites isolated from ascidians of the family Didemnidae. Overall, 81 compounds are presented, displaying great structural diversity and possessing a number of significant biological/pharmacological properties. In addition to the most numerous brominated compounds, chlorinated and iodinated ones were also found. The most prolific genus in regard to the number of published papers and isolated molecules is the genus Didemnum, which was treated separately from the rest of the genera of the ascidian family. The structural complexity of the isolated metabolites prompted a number of synthetic endeavors that not only provided conclusive proof of the structure of the metabolites but also enabled the biological tests and the possible application of these metabolites.

show abstract

“…The total synthesis of the cytotoxic polyketide Biselide E from an Okinawan Didemnid ascidian has recently been achieved [ 81 ].…”

Section: Cyclic Depsipeptides and Polyketidesmentioning

confidence: 99%

Ascidian Toxins with Potential for Drug Development

Watters

2018

Marine Drugs

View full text Add to dashboard Cite

Ascidians (tunicates) are invertebrate chordates, and prolific producers of a wide variety of biologically active secondary metabolites from cyclic peptides to aromatic alkaloids. Several of these compounds have properties which make them candidates for potential new drugs to treat diseases such as cancer. Many of these natural products are not produced by the ascidians themselves, rather by their associated symbionts. This review will focus mainly on the mechanism of action of important classes of cytotoxic molecules isolated from ascidians. These toxins affect DNA transcription, protein translation, drug efflux pumps, signaling pathways and the cytoskeleton. Two ascidian compounds have already found applications in the treatment of cancer and others are being investigated for their potential in cancer, neurodegenerative and other diseases.

show abstract

Total Synthesis of Biselide E, a Marine Polyketide

Cited by 6 publications

References 23 publications

The Tetrahydrofuran Motif in Polyketide Marine Drugs

The Tetrahydrofuran Motif in Polyketide Marine Drugs

Ascidian halogen-containing secondary metabolites from the family didemnidae

Ascidian Toxins with Potential for Drug Development

Contact Info

Product

Resources

About