A stereoselective approach for the southeast segment (C1–C16) of (+)-sorangicin A

Sridhar, Y.; Srihari, P.

doi:10.1039/c3ob40985f

Cited by 18 publications

(11 citation statements)

References 24 publications

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“…With the enantioenriched β-hydroxyester 13 in hand, we proceeded with the Achmatowicz rearrangement 11,17,18 using mCPBA to give the hemiacetal 15 in a diastereomeric ratio of 91 : 9 where the major isomer is presumed to be the one where the hydroxyl group is in the axial position due to the anomeric effect (Scheme 3). The crude mixture of 15 could be reduced 19 to give 16 with 61% unoptimized yield over 2 steps.…”

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confidence: 99%

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Koh

Loh

2015

Green Chem.

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confidence: 99%

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Koh

Loh

2015

Green Chem.

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“…101 The retrosynthetic analysis shows that acetal 120 was planned from furfuryl alcohol 121 using an Achmatowicz reaction.…”

Section: Introductionmentioning

confidence: 99%

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Ghosh

Brindisi

2016

RSC Adv.

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Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable efforts are devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the syntheses of these subunits, there are issues related to regio and stereochemical outcomes, as well as versatility and compatibility of reaction conditions and functional group tolerance. The Achmatowicz reaction, an oxidative ring enlargement of furyl alcohol, was developed in the 1970s. The reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

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“…Smith and co-workers described the first total synthesis and a formal synthesis was disclosed by Crimmins and co-workers . In addition, several groups have reported on the synthesis of different subunits …”

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Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Nyalata

Raghavan

2019

Org. Lett.

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A convergent stereoselective route to the C16–C37 fragment of sorangicin A is disclosed using an α-chloro sulfide for C–C bond formation. The key intermediate, an α,β-unsaturated ketone, is revealed by a [2,3] sigmatropic rearrangement of a propargylic sulfoxide. Three disparate approaches are detailed to create the C25 carbinol stereocenter. The cis-2,6-disubstitution of the THP ring is secured by ionic hydrogenation. A cross-metathesis reaction and Julia–Kocienski olefination furnish the C16–C37 fragment of sorangicin A.

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A stereoselective approach for the southeast segment (C1–C16) of (+)-sorangicin A

Cited by 18 publications

References 24 publications

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

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