Facile enantiospecific synthesis of (+)-iso-cladospolide B

Prasad, Kavirayani R.; Gandi, Vasudeva Rao

doi:10.1016/j.tetasy.2010.01.011

Cited by 17 publications

(6 citation statements)

References 24 publications

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“…The diols were employed in the total synthesis of several natural products including macrolactones such as cladospolides, palmerolide A, microcarpalide and aspercyclide C (Scheme 5). [23–30] …”

Section: Discussionmentioning

confidence: 99%

γ‐Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products

Nanda

Shruthi

Prasad

2021

The Chemical Record

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“Chiral pool” compounds possessing well defined stereocenters and suitable functionality serve as excellent building blocks for the synthesis of natural products and therapeutically important compounds. Tartaric acid is a C2‐symmetric molecule available in both enantiomeric forms. It was extensively utilized in the synthesis of privileged chiral ligands/catalysts such as TADDOLs, and as a start point in the synthesis of plethora of compounds. The advent of several new C−C bond forming reactions offers opportunity for the development of novel synthetic strategies based on chiral pool compounds. We found that the desymmetrization of the bis‐dimethyl amide/Weinreb amide derived from tartaric acid can be accomplished by controlled addition of Grignard /organolithium reagents leading to the mono keto amides, the reduction of which affords the γ‐hydroxy amides. This account describes our research efforts of more than a decade on the synthesis and application of diverse γ‐hydroxy amides derived from tartaric acid in the total synthesis of structurally simple to complex bio‐active natural products.

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Section: Discussionmentioning

confidence: 99%

γ‐Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products

Nanda

Shruthi

Prasad

2021

The Chemical Record

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“…2(5H)-furanones are heterocyclic carbonyl compounds, which are widespread in natural and in synthetic products (Prasad & Gandi, 2010;Steenackers et al, 2010). 5-menthyloxy-3,4-dihalo-2(5H)-furanones, being a kind of chiral synthons, are widely used in asymmetric Michael addition-elimination tandem reactions (Song et al, 2009).…”

Section: S1 Commentmentioning

confidence: 99%

(5S)-3-Chloro-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-4-(4-methylpiperidin-1-yl)furan-2(5H)-one

Wang¹,

Fu²,

Cai³

et al. 2011

Acta Cryst E

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The title compound, C20H32ClNO3, was obtained via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menthyloxy)furan-2(5H)-one and 4-methylpiperidine in the presence of potassium fluoride. The furanone ring is approximately planar [maximum atomic deviation = 0.022 (2) Å] while the cyclohexane ring adopts a chair conformation. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

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“…3 A solitary synthesis of the putative structure 4 and the revised structure 3 of synargentolide A has appeared recently. We have been involved in the synthesis of bio-active lactones from chiral pool tartaric acid 5 and herein we report a facile synthesis of 1a from tartaric acid.…”

Section: Introductionmentioning

confidence: 99%