Total Synthesis of (−)-Angiopterlactone B

Thomson, Marie I.; Nichol, Gary S.; Lawrence, Andrew L.

doi:10.1021/acs.orglett.7b00929

Cited by 34 publications

(22 citation statements)

References 17 publications

(16 reference statements)

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“…The Achmatowicz rearrangement product 138 can then be generated without loss of enantiopurity (Figure 34). This strategy was recently applied to the synthesis of (−)‐Angiopterlactone B ( 140 ) in four steps from 2‐acetylfuran 136 by Lawrence et al [58] . The Achmatowicz rearrangement product 138 was converted to the lactone 139 via a non‐trivial but well understood and practical iridium‐catalyzed dynamic kinetic isomerization [59] .…”

Section: Synthesis Of Three‐dimensional Scaffoldsmentioning

confidence: 99%

Escaping from Flatland: Stereoconvergent Synthesis of Three‐Dimensional Scaffolds via Ruthenium(II)‐Catalyzed Noyori–Ikariya Transfer Hydrogenation

Cotman

2020

Chemistry A European J

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Noyori-Ikariya-type ruthenium(II)-catalysts for asymmetric transfer hydrogenation(ATH) have been known for 25 years and have proved asawell-behaved and userfriendly platform for the synthesis of chiral secondary alcohols. Ap rogress has been made in the past five years in understanding the asymmetric reduction of complex ketones, where up to four stereocenters can be controlled in as ingle chemical transformation. Intriguing multi-chiral molecular architecturesa re therefore available in few well understood and robusts ynthetic steps from commerciallya vailable buildingb locks and possessh andles for additional functionalization. The aim of this Review is to showcase the availability of three-dimensional scaffolds and homochiral lead-like compounds via ATHa nd inspiret heir direct use in drug discovery endeavors. Basic mechanistic insights are provided to demystifyt he stereo-chemical outcomes, as well as examples of diastereoselective transformationso fe nantiopure alcohols to give af eeling of how these rigid non-planar molecules can be further elaborated.

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Section: Synthesis Of Three‐dimensional Scaffoldsmentioning

confidence: 99%

Escaping from Flatland: Stereoconvergent Synthesis of Three‐Dimensional Scaffolds via Ruthenium(II)‐Catalyzed Noyori–Ikariya Transfer Hydrogenation

Cotman

2020

Chemistry A European J

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“…Lawrence and colleagues reported a total synthesis of angiopterlactone B, in which target molecule was achieved from 7 in one step by the isomerisation followed by oxa‐Michel addition using K 2 CO 3 .…”

Section: Resultsmentioning

confidence: 99%

Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root

et al. 2018

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Formal synthesis of angiopterlactone B has been accomplished via. enantioselective reduction of ketone with Daucus carota, Sharpless dihydroxylation and Andos modified Horner‐Wadsworth‐Emmons (HWE) reagent to introduce Z‐olefination. Here we evolved a new path for the synthesis of (S,S)‐osmundalactone and 3–5 dihydroxy γ‐caprolactone. The initial synthetic route for both caprolactone and osmundalcactone build on biocatalytic process while in later case Sharpless dihydroxylation delivered required stereocentres. Z‐selective olefination was utilized to furnish caprolactone which was further recycled in to 1‐(5‐oxotetrahydrofuran‐2yl) ethyl 2‐phenyl acetate. Both synthetic routes found to be applicable for many synthetic reactions.

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“…We also found that a dynamic kinetic stereoselective isomerization of the same lactol could be realized in the presence of an iridium catalyst and acid additives (Scheme B) . This stereoselective isomerization was recently applied to the total synthesis of natural product angiopteralactone B . In this update, we will describe a new type of dynamic kinetic stereoselective process ‐ an Ir‐catalyzed allylic etherification reaction, which is shown in Scheme C.…”

Section: Methodsmentioning

confidence: 99%

Iridium‐Catalyzed Dynamic Kinetic Stereoselective Allylic Etherification of Achmatowicz Rearrangement Products

et al. 2017

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We recently developed a novel Ir-catalyzed dynamic kinetic isomerization reaction for Achmatowicz rearrangement products. In this update, we show that products derived from the Achmatowicz rearrangement can also undergo Ircatalyzed dynamic kinetic allylic etherification in the presence of an appropriate ligand and additive to afford useful intermediates for the synthesis of carbohydrates. The addition of the triphenyl phosphite ligand shuts down the isomerization pathway and promotes the allylic etherification pathway. The addition of diphenyl phosphate improved the diastereoselectivity for the addition reaction. Interestingly, opposite diastereoselectivity was observed for sterically demanding alcohol nucleophiles compared to less sterically demanding alcohol nucleophiles. The method was also applied to the synthesis of several 2,3-dideoxypyranosides.

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Total Synthesis of (−)-Angiopterlactone B

Cited by 34 publications

References 17 publications

Escaping from Flatland: Stereoconvergent Synthesis of Three‐Dimensional Scaffolds via Ruthenium(II)‐Catalyzed Noyori–Ikariya Transfer Hydrogenation

Escaping from Flatland: Stereoconvergent Synthesis of Three‐Dimensional Scaffolds via Ruthenium(II)‐Catalyzed Noyori–Ikariya Transfer Hydrogenation

Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root

Iridium‐Catalyzed Dynamic Kinetic Stereoselective Allylic Etherification of Achmatowicz Rearrangement Products

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