Total Synthesis of (−)-Mitrephorone A

Richter, Matthieu J. R.; Schneider, M.; Brandstätter, Marco; Krautwald, Simon; Carreira, Erick M.

doi:10.1021/jacs.8b09685

Cited by 55 publications

(39 citation statements)

References 81 publications

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“…Richter et al [83] reported the first and enantioselective synthesis of (−)-mitrephorone A in 2018 by using a novel late-stage oxidative cyclisation (Scheme 7). Synthesis commenced with methacrolein 28 and gave 29 in steps.…”

Section: Oxetanesmentioning

confidence: 99%

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Harmalkar

Choi

et al. 2019

Molecules

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Saturated oxygen heterocycles are widely found in a broad array of natural products and other biologically active molecules. In medicinal chemistry, small and medium rings are also important synthetic intermediates since they can undergo ring-opening and -expansion reactions. These applications have driven numerous studies on the synthesis of oxygen-containing heterocycles and considerable effort has been devoted toward the development of methods for the construction of saturated oxygen heterocycles. This paper provides an overview of the biological roles and synthetic strategies of saturated cyclic ethers, covering some of the most studied and newly discovered related natural products in recent years. This paper also reports several promising and newly developed synthetic methods, emphasizing 3–7 membered rings.

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Section: Oxetanesmentioning

confidence: 99%

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Harmalkar

Choi

et al. 2019

Molecules

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“…The direct α-acetoxylation of ketones provides an efficient and synthetically practical method for α-oxygen functionalization of carbonyl compounds, which exhibits various applications as synthetic key precursors and versatile synthons in organic synthesis (Mizukami et al, 1978 ; Hecker and Werner, 1993 ; Varma et al, 1998 ; Kaila et al, 2007 ; Edwards et al, 2008 ; Richter et al, 2018 ; Huang et al, 2019 ). Therefore, considerable efforts have been made in the development of synthetic protocols for α-acetoxylation of ketones ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Hypervalent Iodine-Mediated Diastereoselective α-Acetoxylation of Cyclic Ketones

et al. 2020

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A binary hybrid system comprising a hypervalent iodine(III) reagent and BF 3 •OEt 2 Lewis acid was found to be effective for the diastereoselective α-acetoxylation of cyclic ketones. In this hybrid system, BF 3 •OEt 2 Lewis acid allowed the activation of the hypervalent iodine(III) reagent and cyclic ketones for smooth α-acetoxylation reaction, achieving high diastereoselectivity. This hypervalent iodine-mediated α-acetoxylation of the cyclic ketone reaction plausibly undergoes an S N 2 substitution mechanism via an α-C-bound hypervalent iodine intermediate. The diastereoselectivity of the reaction mainly originates from thermodynamic control.

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“…We have previously reported the first and enantioselective total synthesis of (−)-mitrephorone A ( 1 ), which lacked diastereocontrol. 3 Herein, we report a new route for a highly enantio- and diastereoselective synthesis of 1 . Our retrosynthetic analysis involved disconnection of (−)-mitrephorone A ( 1 ) to 2 ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%