Total Synthesis of (+)-Aplykurodinone-1

Xu, Bo; Xun, Wen; Wang, Tingzhong; Qiu, Fayang G.

doi:10.1021/acs.orglett.7b02350

Cited by 9 publications

(6 citation statements)

References 29 publications

(12 reference statements)

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“…The presence of a vinylic methyl group enhances the chemoselectivity of the ATH reaction. These chiral cyclohexanols are useful platforms for the synthesis of more elaborate products [ 26 , 27 , 28 ]. The ATH reaction has also been studied on cycloalkenones, with five- and seven-membered rings obtaining lower values of enantio- and chemoselectivity (see the Supplementary Materials ).…”

Section: Resultsmentioning

confidence: 99%

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Jurado

Domı́nguez-Pérez

Illa

et al. 2022

IJMS

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The enantioselective preparation of the two isomers of 4-hydroxy-2-cyclohexanone derivatives 1a,b was achieved, starting from a common cyclohexenone, through asymmetric transfer hydrogenation (ATH) reactions using bifunctional ruthenium catalysts. From these versatile intermediates, a stereoselective route to a cytosine analogue built on a bicyclo [4.1.0]heptane scaffold is described. Nucleoside kinase activity assays with this cyclopropyl-fused cyclohexane nucleoside, together with other related nucleosides (2a–e), were performed, showing that thymine- and guanine- containing compounds have affinity for herpes simplex virus Type 1 (HSV-1) thymidine kinase (TK) but not for human cytosolic TK-1, thus pointing to their selectivity for herpetic TKs but not cellular TKs.

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Section: Resultsmentioning

confidence: 99%

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Jurado

Domı́nguez-Pérez

Illa

et al. 2022

IJMS

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“…Similar convergent pathways, utilizing a variety of novel strategies and methods, have been reported by five other research groups . Recently, Qiu and co-workers described a de novo synthesis in which the C11 side chain was constructed by using an Ireland–Claisen rearrangement of a ketene silyl acetal formed from naturally occurring ( R )-seudenol and ( R )-citronellic acid, thus avoiding a cumbersome conjugate-addition-based process …”

mentioning

confidence: 76%

H-Bonding Mediated Asymmetric Intramolecular Diels–Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1

Lee

Cho

2018

Org. Lett.

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An asymmetric formal total synthesis of (+)-aplykurodinone-1 was achieved using a route, in which hydrogen bonding serves as a stereochemical control element governing the π-facial selectivity of intramolecular Diels–Alder (IMDA) reaction of an enone tethered 2-pyrone. In the IMDA process, the configuration at a stereogenic, hydroxyl bearing an α-carbon in the enone dienophile is conveyed in a highly effective manner through intramolecular hydrogen bonding with the enone carbonyl oxygen. The tricyclic lactone, generated in this process, was successfully converted to a late stage intermediate in Danishefsky’s synthesis of aplykurodinone-1.

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“…Later in 2017, the Qiu group finished a novel asymmetric total synthesis of (+)‐aplykurodinone‐1, [37] the synthetic strategy of which was distinctive from those reported (Scheme 9). The key steps involved an Ireland‐Claisen rearrangement, an intramolecular carbonyl‐ene cyclization and an intramolecular Michael addition.…”

Section: The Synthetic Approaches Toward Aplykurodinone‐1mentioning

confidence: 99%

Synthetic Approaches of Aplykurodinone‐1: A Minireview

Xun

2022

Asian J Org Chem

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Aplykurodinone‐1, a marine steroid with intriguing molecular architecture and promising biological activities, has captured the attention of many synthetic chemists. In this paper we have overviewed the synthetic approaches of aplykurodinone‐1 to date, with a focus on the novel strategies utilized to improve the synthetic efficiency. This review summarizes the contribution of different research groups in the total or formal synthesis of aplykurodinone‐1 in either racemic or enantiomeric form.

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Total Synthesis of (+)-Aplykurodinone-1

Cited by 9 publications

References 29 publications

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

H-Bonding Mediated Asymmetric Intramolecular Diels–Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1

Synthetic Approaches of Aplykurodinone‐1: A Minireview

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