First synthesis of (<i>S</i>)-(+)-hymenoic acid, a DNA polymerase λ inhibitor isolated from <i>Hymenochaetaceae</i> sp

Takahashi, Kensuke; Matsui, Miki; Kuse, Masaki; Takikawa, Hirosato

doi:10.1080/09168451.2017.1406302

Cited by 5 publications

(3 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is generally accepted that the stereoselectivity for the preparation of trisubstituted alkenes via a Julia-Kocienski olefination is modest . In fact, there are a few recent examples in which methyldialkyl alkenes were obtained with notable E -diastereoselectivity, − but those results cannot clearly justify the adoption of certain rules regarding the base and/or solvent used. Certainly, other structural features of coupling partners may play a crucial role in the outcome of each reaction.…”

Section: Resultsmentioning

confidence: 99%

“…R f = 0.57 (n-hexane/EtOAc, 3:1). 1 1-O-Triethylsilyl-2,3-O-isopropylidene-2-C-methyl-D-erythrofuranose (24). A THF (127 mL) solution of 23 (29.105 g, 63.47 mmol, 1 equiv) in a two-neck 1 L round-bottom flask outfitted with an equalpressure dropping funnel was heated at 66 °C, and a solution of lithium triethylborohydride in THF (1.0 M, 158.7 mL, 158.7 mmol, 2.5 equiv) was added dropwise over a 30 min period via the dropping funnel.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 1 more Smart Citation

Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

2021

View full text Add to dashboard Cite

The total synthesis of cytotoxic meroditerpenoid naphthoquinone derivative chabrolonaphthoquinone B (1) in an enantiospecific manner is divulged using a chiral pool approach. The key step of our synthetic route is a modified Julia olefination between a sulfone-bearing aliphatic fragment and a Diels–Alder-derived aromatic aldehyde, leading to the stereoselective construction of the E-trisubstituted double bond.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

2021

View full text Add to dashboard Cite

show abstract

“…Takahashi et al . accomplished the synthesis of S‐(+)‐Hymenoic acid 268 for the first time [73] . Julia olefination of sulfone 265 with aldehyde 266 using LiHMDS in THF as a solvent, followed by the deprotection of silyl group afforded the desired product 267 (E/Z=4:1)as the key intermediate in the synthesis of 268 (Scheme 50).…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

Recent Applications and Trends in the Julia‐Kocienski Olefination

Rinu¹,

Radhika²,

Anilkumar³

2022

ChemistrySelect

View full text Add to dashboard Cite

The Julia-Kocienski (J-K) olefination is a modified version of Julia-Lythgoe olefination. In this reaction, an aldehyde or ketone is coupled with heterocycle-bearing sulfone in the presence of a strong base to yield alkene. It has shown wide application in the synthesis of olefinic fragments in natural product synthesis. The Julia-Kocienski olefination is one of the most efficient protocols for the synthesis of E-alkenes. Nowa-days, a variety of natural products were synthesised by using the Julia-Kocienski olefination as the key step, and several developments and modifications were witnessed in this area. This review comprehends the recent developments and achievements in Julia-Kocienski olefination along with its application in natural product synthesis covering literature from 2016 to 2021.

show abstract

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Ouzounthanasis,

Rizos,

Koumbis

2023

Eur J Org Chem

View full text Add to dashboard Cite

Julia‐Kocienski olefination, a coupling reaction between a carbonyl component and a sulfone partner, has been emerged as a powerful synthetic tool in the preparation of several organic compounds. A number of interesting examples involving particularly the preparation of trisubstituted alkenes along with important observations regarding the stereoselectivity of those reactions have been recently reported. This reviewing work covers the literature for the period 2016‐2022 and describes in a comprehensive way the progress and developments of Julia‐Kocienski olefination application in the synthesis of trisubstituted alkenes which serve as precursors of natural products and their analogs as well of pharmaceutically interesting/biologically important compounds. Moreover, key methodology results dealing with the investigation of the optimum conditions and stereoselectivities and new modifications and approaches are discussed.

show abstract

First synthesis of (S)-(+)-hymenoic acid, a DNA polymerase λ inhibitor isolated from Hymenochaetaceae sp

Cited by 5 publications

References 18 publications

Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

Recent Applications and Trends in the Julia‐Kocienski Olefination

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

Contact Info

Product

Resources

About