Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts

Huang, Jianguo; Shia, Kak‐Shan

doi:10.1021/acs.orglett.1c01807

Cited by 2 publications

(1 citation statement)

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“…The above results clearly demonstrate that this newly developed Diels–Alder approach in combination with an appropriate Lewis acid has great potential in synthesizing natural and non-natural polyketides containing a 4,4-dimethyl-1-tetralone unit. Meeting significant success in serving compound 2 ~ 8 as dienophiles, we further extended the methodology to dienophile 9 activated with an aldehyde group instead of an ester group [ 25 ]. Not unexpectedly, Diels–Alder reactions of 9 with various dienes tested in Table 2 under similar reaction conditions also gave rise to corresponding Diels–Alder adducts in moderate to good yields (63~90%, unpublished results).…”

Section: Resultsmentioning

confidence: 99%

A Convenient Diels-Alder Approach toward Potential Polyketide-like Antibiotics Using α-Activated α,β-Unsaturated 4,4-Dimethyl-1-tetralones as Dienophiles

et al. 2023

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Making use of a Diels–Alder approach based on various α,β-unsaturated 2-carbomethoxy-4,4-dimethyl-1-tetralones as novel dienophiles, the corresponding polycyclic adducts could be efficiently synthesized in good to high yields (74~99%) in the presence of Lewis acid (e.g., SnCl4). Accordingly, a synthetically useful platform is established to provide a focused aromatic polyketide-like library for screening of potential natural and non-natural antimicrobial agents.

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Section: Resultsmentioning

confidence: 99%

A Convenient Diels-Alder Approach toward Potential Polyketide-like Antibiotics Using α-Activated α,β-Unsaturated 4,4-Dimethyl-1-tetralones as Dienophiles

et al. 2023

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Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones

Mousavi,

Di Mola,

Pierri

et al. 2024

J. Org. Chem.

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Herein we report two processes facilitated by diisopropylethylamine (DIPEA) for the synthesis of novel bridged polycyclic molecule analogues to natural products. The use of 4-bromoisochroman-3-one initiated an autoxidation reaction, followed by a Diels−Alder cycloaddition in the presence of electron-deficient dienophiles. Mechanistic studies revealed isochromane-3,4dione as a key intermediate, which undergoes in situ dienolization/dearomatization followed by a [4 + 2] cycloaddition. Subsequently, the synthesis and direct application of isochromane-3,4-diones in the Diels−Alder reaction enabled the development of an alternative method with an enhanced efficiency and improved atom economy. In addition to chalcones, other enones and common electron-poor alkenes, bearing ester, nitro and cyano electron-withdrawing groups (including both terminal, cis acyclic and cyclic alkenes), were successfully reacted. The mechanism was also investigated, and a subsequent reductive ring opening was successfully carried out.

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Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts

Cited by 2 publications

References 40 publications

A Convenient Diels-Alder Approach toward Potential Polyketide-like Antibiotics Using α-Activated α,β-Unsaturated 4,4-Dimethyl-1-tetralones as Dienophiles

A Convenient Diels-Alder Approach toward Potential Polyketide-like Antibiotics Using α-Activated α,β-Unsaturated 4,4-Dimethyl-1-tetralones as Dienophiles

Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones

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