Asymmetric synthesis of the C(6–18) bis(tetrahydropyran)spiroacetal fragment of the lituarines

Robertson, Jeremy; North, C.; Sadig, Jessie E. R.

doi:10.1016/j.tet.2011.03.116

Cited by 21 publications

(8 citation statements)

References 84 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…of other alkene bonds in the precursor. In a recent study directed towards the synthesis of the tricyclic spiroacetal unit in the lituarine family of marine metabolites, for example, Robertson et al 59 found that whereas the furfuryl alcohol 126 underwent the expected Achmatowicz reaction in the presence of VO(acac) 2 -tBuO 2 H leading to 125, use of MCPBA instead gave largely the spiroacetal 127. Nevertheless, in spite of a few limitations the products of Achmatowicz reactions have been widely used in the synthesis of a range of target structures including heterocyclic natural products 60 and oligosaccharides.…”

Section: Oxidative Cleavage Of Furfuryl Alcohols and The Achmatowicz ...mentioning

confidence: 99%

The versatility of furfuryl alcohols and furanoxonium ions in synthesis

Palframan

Pattenden

2014

Chem. Commun.

View full text Add to dashboard Cite

Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis. They are precursors to furanoxonium ion intermediates which are implicated in the Piancatelli reaction (leading to 2-cyclopentenones) and in the synthesis of novel dihydrofuran-based exo enol ether/cyclic ketal natural products. They are also intermediates in a recently discovered (4+3) cycloaddition reaction with 1,3-dienes leading to furan ring-fused cycloheptenes. Here we provide a perspective on recent developments in these areas of synthesis, alongside recent applications of the Achmatowicz reaction and [5+2] cycloaddition reactions of the resulting oxidopyrylium ions.

show abstract

Section: Oxidative Cleavage Of Furfuryl Alcohols and The Achmatowicz ...mentioning

confidence: 99%

The versatility of furfuryl alcohols and furanoxonium ions in synthesis

Palframan

Pattenden

2014

Chem. Commun.

View full text Add to dashboard Cite

show abstract

“…With access to the target hydroxy ketone 8 secured, investigations into the necessary diastereoselective reduction of the ketone were next undertaken (Scheme ). Borohydride reduction of 8 in the presence of zinc chloride or cerium chloride heptahydrate as chelating reagents afforded the separable epimeric diols 17a and 17b in a 2:1 to 3:1 ratio, in high yields (Table , entries 1–3). Zinc borohydride was found to give an improved ratio of diastereomers (4.5:1) in 80% yield (Table , entry 4).…”

mentioning

confidence: 99%

General Synthesis of the Nitropyrrolin Family of Natural Products via Regioselective CO₂-Mediated Alkyne Hydration

2017

View full text Add to dashboard Cite

The total synthesis of the 2-nitropyrrole natural products nitropyrrolins A and B and the formal synthesis of nitropyrrolin D are reported. The key 2-nitro-4-alkylpyrrole core was efficiently assembled by Sonogashira cross-coupling, with complete control of regioselectivity. An unusual carboxylative cyclization, sulfonylcarbamate formation, and base-promoted cleavage sequence enabled access to the key hydroxy ketone without affecting the protected 2-nitropyrrole unit. The total synthesis provides a general approach for preparation of the bioactive nitropyrrolin family of natural products.

show abstract

“…In addition, they possess an exocyclic dienamide moiety (Figure ). Robertson worked on the synthesis of these complex compounds, achieving partial synthesis of the proposed structures. Smith III , achieved the total synthesis of the proposed structures of lituarines B and C and upon comparison of synthetic, and isolated compounds stated that the proposed stereochemistry was erroneous.…”

Section: Overall Of Thf-containing Macrolidesmentioning

confidence: 99%