Ti-based subunit couplings: a concise, modular synthesis of routiennocin methyl ester

McCabe, Jamie M.; Phillips, Andrew J.

doi:10.1016/j.tet.2013.04.105

Cited by 16 publications

(5 citation statements)

References 24 publications

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“…This general strategy was also applied by the same group in their 2008 synthesis of the C 1 –C 23 fragment of spirastrellolide B (Scheme ) as well as their 2013 synthesis of routiennocin methyl ester (Scheme ). − Cyclopropyl alcohol ring opening has also been used by Ding and co-workers in their recent publication on the total synthesis of rhodomolleins XX and XXII …”

Section: C–c Bond Cleavage To Generate β-Keto Radicalsmentioning

confidence: 98%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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The carbon–carbon (C–C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C–C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C–C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor–acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.

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Section: C–c Bond Cleavage To Generate β-Keto Radicalsmentioning

confidence: 98%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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“…We have tried to extract the strategic disconnections toward the carbon skeletons and key methods involved in the construction of the structural subunits, rather than comprehensively detailing every synthetic step from all the different approaches. A compilation of synthetic studies on other carboxyl polyether ionophore natural products completed in the time period from 2001 to 2018 is given in Table S1 (Supporting Information) with key transformations highlighted …”

Section: Recent Progress In the Synthesis Of Polyether Ionophores: Zimentioning

confidence: 99%

Chemical Syntheses and Chemical Biology of Carboxyl Polyether Ionophores: Recent Highlights

2019

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“…Phillips and co-workers employed the iron-initiated fragmentation of a cyclopropanol as part of a reductive coupling of 132-1 and 132-2 en route to routiennocin methyl ester 132-4 (Scheme 132). 716 Initially, cyclopropanol 132-3 was constructed using Cha's terminal olefin modification 717 of the Kulinkovich cyclopropanation. 718 When the reductant was cyclohexylmagnesium bromide, 132-3 was obtained in 37% yield.…”

Section: Oxidative Ring Fragmentationmentioning

confidence: 99%

Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis

2017

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First-row transition-metal-mediated reactions constitute an important and growing area of research due to the low cost, low toxicity, and exceptional synthetic versatility of these metals. Currently, there is considerable effort to replace existing precious-metal-catalyzed reactions with first-row analogs. More importantly, there are a plethora of unique transformations mediated by first-row metals, which have no classical second- or third-row counterpart. Herein, the application of first-row metal-mediated methods to the total synthesis of natural products is discussed. This Review is intended to highlight strategic uses of these metals to realize efficient syntheses and highlight the future potential of these reagents and catalysts in organic synthesis.

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Ti-based subunit couplings: a concise, modular synthesis of routiennocin methyl ester

Cited by 16 publications

References 24 publications

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

Chemical Syntheses and Chemical Biology of Carboxyl Polyether Ionophores: Recent Highlights

Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis

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