Total Synthesis of the Marine Polyketide (−)-Gracilioether F

Datta, Ritabrata; Ghosh, Subrata

doi:10.1021/acs.joc.7b01179

Cited by 10 publications

(1 citation statement)

References 33 publications

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“…[54] [57] The first asymmetric synthesis of (À )-gracilioether F (203) was achieved by Datta and Ghosh through a chiron approach and pivoted on a crucial intramolecular radical cyclization to assemble a key bicyclic lactone intermediate (253!254, Scheme 24). [57] Starting from D-mannitol derived acetonide ester 248, catalytic hydrogenation to 249, followed by divinylation of the ester and O-allylation of the resulting divinyl carbinol produced 250. RCM with Grubbs-I catalyst and PDC oxidation led to an inseparable mixture of butenolides 251 a,b.…”

Section: Total Synthesis Of Furo[34-b]furan-2(3h)-one Natural Product...mentioning

confidence: 99%

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

2020

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Complex, functionally embellished natural products embodying diverse, oxygen rich furofuranone fragments like furo[3,4-c]furanone, furo[2,3-b]furanone, furo[3,4-b]furan-2(3H)-one, furo[3,4-b]furan-4(2H)-one and furo[3,4-b]furan-6(4H)-one as the key motif and displaying wide range of biological activities such as anti-cancer, anti-HIV, anti-microbial activities, etc., continue to draw considerable traction towards targeted synthesis, methodolgical developments as well as medicinal chemistry guided efforts. The challenging and tempting combination of complexity laden architecture and varied bioactivity profile, among the variegated furofuranone natural products has led to intense synthetic activity in the arena in recent years and culminated in the total synthesis of structurally diverse family of bioactive metabolites such as gracilioethers, syringolides, degraded spongianes etc. While comprehensively recounting the attainments in the total syntheses of furofuranone natural products in the past two decades (in the 21st century), this review attempts to identify the key tactics deployed in each synthetic campaign. This topical review aims at drawing and sustaining the interest of synthetic chemistry community in undertaking further creative pursuits towards this rich and enticing family of natural products while concurrently exploring the utility driven diversity space around them. Scheme 2. Pattenden's synthesis of (�)-anthecularin (ref. 11) Scheme 3. Watanabe's synthesis of (+)-anthecularin (ref. 12

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Section: Total Synthesis Of Furo[34-b]furan-2(3h)-one Natural Product...mentioning

confidence: 99%

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

2020

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Ring‐Opening Reactions of Epoxides With Titanium(III) Reagents

RajanBabu¹,

Nugent²,

Halder³

2022

Organic Reactions

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The ring‐opening reactions of epoxides with titanium(III) reagents such as Cp 2 TiCl are critically reviewed, including the scope, limitations, and mechanism of these synthetically useful transformations. The initial reaction proceeds by single‐electron transfer to give a carbon‐centered β‐titanoxy radical. The resulting radical can be terminated by a number of different reaction pathways, including epoxide deoxygenation, reduction to the alcohol, intermolecular addition to activated olefins, and intramolecular addition (cyclization). The literature is surveyed from the first reported examples in 1988 through October, 2021.

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