(π-Allyl)tricarbonyliron Lactone Complexes in Organic Synthesis:  A Useful and Conceptually Unusual Route to Lactones and Lactams

Ley, Steven V.; Cox, Liam R.; Meek, Graham

doi:10.1021/cr950015t

Cited by 108 publications

(47 citation statements)

References 72 publications

(100 reference statements)

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“…[12] Herein we present a ligand-dependent mechanistic dichotomy in iron-catalyzed allylic substitution, which not only fulfils the requirements mentioned in (a) and (b) above, but also allows the reaction to follow the unprecedented pallyl iron mechanism (c). The latter aspect represents one of the basic requirements for the development of an asymmetric allylic substitution.…”

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confidence: 79%

Ligand‐Dependent Mechanistic Dichotomy in Iron‐Catalyzed Allylic Substitutions: σ‐Allyl versus π‐Allyl Mechanism

et al. 2007

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confidence: 79%

Ligand‐Dependent Mechanistic Dichotomy in Iron‐Catalyzed Allylic Substitutions: σ‐Allyl versus π‐Allyl Mechanism

et al. 2007

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“…Construction of the C10-C20 lactone 142: The construction of the last remaining major fragment of rapamycin afforded us an opportunity to demonstrate the utility of iron carbonyl methodology developed within our group [79] for construction of the key d-lactone moiety.…”

Section: Synthesis Of Vinyl Bromide 69mentioning

confidence: 99%

Total Synthesis of Rapamycin

Ley

Tackett

Maddess

et al. 2009

Chemistry A European J

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For over 30 years, rapamycin has generated a sustained and intense interest from the scientific community as a result of its exceptional pharmacological properties and challenging structural features. In addition to its well known therapeutic value as a potent immunosuppressive agent, rapamycin and its derivatives have recently gained prominence for the treatment of a wide variety of other human malignancies. Herein we disclose full details of our extensive investigation into the synthesis of rapamycin that culminated in a new and convergent preparation featuring a macro-etherification/catechol-templating strategy for construction of the macrocyclic core of this natural product.

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“…The regiochemical outcome of this reaction was explained in terms of steric shielding of ligand 23 in the reacting p-allylpalladium complex. Vinyloxiranes can also be converted into b-lactones (Scheme 9.30) [133,134]. Opening of 66 with Fe 2 (CO) 9 resulted in the (p-allyl)tricarbonyliron derivative 67 in good yield, together with a minor diastereomer (not shown).…”

Section: S N 2 Additionsmentioning

confidence: 99%