We have used extensively ironbicarbonyl lactone and lactic complexes as a conceptually new bond forming process to lactones, lactams. These complexes also served as key entry points to 1,5 and 1,7 remote control and as precursors to various natural products.
See π-Allyltricarbonyliron lactone complexes in organic synthesis: a useful and conceptually unusual route to lactones and lactams S.V. Ley, L.R. Cox, G. Meek, Chem. Rev. 1996, 96, 423-442.
Related Publications:
- Tetracyanoethylene addition to iron tricarbonyl complexes of substituted cyclooctatetraenes. Regioselectivity considerations during formation of the 2,3,4,10-tetrahapto adducts L.A. Paquette, S.V. Ley, S. Maiorana, D.F. Schneider, M.J. Broadhurst, R.A. Boggs, J. Am. Chem. Soc. 1975, 97, 4658-4667.
- The formation of unusual sultones during the rearrangement reactions of bicyclic ketones D.S. Brown, H. Heaney, S.V. Ley, K.G. Mason, P. Singh, Tetrahedron Lett. 1978, 41, 3937-3940.
- Isolation characterisation and oxidation of isomeric ferralactone complexes G.D. Annis, S.V. Ley, R. Sivaramakrishnan, A.M. Atkinson, D. Rogers, D.J. Williams, J. Organometallic Chem. 1979, 182, C11-C14.
- Formation of β-lactams from tricarbonyliron lactones complexes G.D. Annis, E.M. Hebblethwaite, S.V. Ley, J. Chem. Soc., Chem. Commun. 1980, 297-298.
- Thermal decomposition of tricarbonyliron lactone complexes G.D. Annis, S.V. Ley, C.R. Self, R. Sivaramakrishnan, J. Chem. Soc., Chem. Commun. 1980, 299-299.
- Preparation of lactones via tricarbonyliron lactone complexes G.D. Annis, S.V. Ley, C.R. Self, R. Sivaramakrishnan, J. Chem. Soc., Perkin Trans. 1 1981, 270-277.
- Thermal rearrangement reactions of tricarbonyliron lactone complexes G.D. Annis, S.V. Ley, C.R. Self, R. Sivaramakrishnan, D.J. Williams, J. Chem. Soc., Perkin Trans. 1 1982, 1355-1361.
- Synthesis of β-lactams from π-allyltricarbonyliron lactone complexes G.D. Annis, E.M. Hebblethwaite, S.T. Hodgson, D.M. Hollinshead, S.V.Ley, J. Chem. Soc., Perkin Trans. 1 1983, 2851-2856.
- π-Allyltricarbonyliron lactone complexes in synthesis: application to the synthesis of the β-lactam antibiotic (+)-thienamycin S.T. Hodgson, D.M. Hollinshead, S.V. Ley, J. Chem. Soc., Chem. Commun. 1984, 494-496.
- Fe2(CO)9 in tetrahydrofuran or under sonochemical conditions as convenient routes to π-allyltricarbonyliron lactone complexes A.M. Horton, D.M. Hollinshead, S.V. Ley, Tetrahedron 1984, 40, 1737-1742.
- Natural product synthesis via π-allyltricarbonyliron lactone complexes G.D. Annis, E.M. Hebblethwaite, S.T. Hodgson, A.M. Horton, D. M. Hollinshead, S.V. Ley, C.R. Self, R. Sivaramakrishnan, 2nd SCI/RSC Medicinal Chemistry Symposium. Special Publication, No. 50, 1984, 148-161.
- Natural product synthesis using π-allyltricarbonyliron lactone complexes: synthesis of parasorbic acid, the carpenter bee pheromone and malyngolide A.M. Horton and S.V. Ley, J. Organometallic Chem. 1985, 285, C17-C20.
- Use of π-allyltricarbonyliron lactam complexes in the preparation of nocardicin derivatives: synthesis of (–)-3-oxo-1-[(p-benzyloxyphenyl)-benzyloxycarbonylmethyl]azetidin-2-one S.T. Hodgson, D.M. Hollinshead, S.V. Ley, C.M.R. Low, D.J. Williams. J. Chem. Soc., Perkin Trans. 1 1985, 2375-2381.
- Synthesis of the β-lactam antibiotic (+)-thienamycin via an intermediate π-allyltricarbonyliron lactone complex S.T. Hodgson, D.M. Hollinshead, S.V. Ley, Tetrahedron 1985, 41, 5871-5878.
- Application of ultrasound to the preparation of tricarbonyliron diene complexes S.V. Ley, C.M.R. Low, A.D. White, J. Organometallic Chem. 1986, C13-C16.
- Organic synthesis with tricarbonyliron lactone complexes S.V. Ley, Phil. Trans. R. Soc. Lond. 1988, 326, 633-640.
- Alkenylcyclic sulphites as novel precursors for the preparation of pi-allyltricarbonyliron lactone complexes M. Caruso, J.G. Knight and S.V. Ley, Synlett, 1990, 224.
- Assessment of butene-1,4-diols as starting materials for the preparation of p-allyltricarbonyliron lactone complexes R.W. Bates, D. Diez-Martin, W.J. Kerr. J.G. Knight, S.V. Ley And A. Sakellaridis, Tetrahedron, 1990, 46, 4063.
- Total synthesis of avermectin B1a: synthesis of the C11-C25 spiroacetal fragment D. Díez-Martín, P. Grice, H.C. Kolb, S.V. Ley, A. Madin, Synlett 1990, 326-328.
- Synthesis of the β-lactone esterase inhibitor valilactone using π-allyltricarbonyliron lactone complexes R.W. Bates, R. Fernández-Moro, S.V. Ley, Tetrahedron Lett.1991, 32, 2651.
- Total synthesis of the anthelmintic macrolide avermectin B1a S.V. Ley, A. Armstrong, D. Díez-Martín, M.J. Ford, P. Grice, J. Knight, H.C. Kolb, A. Madin, C.A. Marby, S. Mukherjee, A.N. Shaw, A.M.Z. Slawin, S. Vile, A.D. White, D.J. Williams, M.Woods, J. Chem. Soc., Perkin Trans. 1 1991, 667-692.
- The use of p-allyltricarbonyliron lactone complexes in the synthesis of b-lactone esterase inhibitor (–)-valilactone R.W. Bates, R. Fernández-Moro and S.V. Ley, Tetrahedron, 1991, 47, 9929.
- Synthesis of the alkaloids (−)-heliotridane and (−)-isoretronecanol via π-allyltricarbonyliron lactam complexes G. Knight and S.V. Ley, Tetrahedron Lett. 1991, 32, 7119.
- Total synthesis of ionophore antibiotic CP-61,405 (routiennocin) D. Díez-Martin, N.R. Kotecha, S.V. Ley, S. Mantegani, J.C. Menéndez, H.M. Organ, A.D. White, B.J. Banks, Tetrahedron, 1992, 48, 7899.
- Tricarbonyliron lactone complexes in organic synthesis S.V. Ley, Pure and Appl. Chem. 1994, 66, 1415.
- Diastereoselective addition reactions to carbonyl groups in the side-chain of p-allyltricarbonyliron lactone complexes S.V. Ley, G. Meek, K-H Metten, C. Pique, J. Chem. Soc., Chem. Commun. 1994, 1931.
- Diastereoselective additions to aldehyde groups in the side-chain of π-allyltricarbonyliron lactone complexes S.V. Ley and G. Meek, J. Chem. Soc., Chem. Commun. 1996, 317-318.
- π-Allyltricarbonyliron lactone complexes in organic synthesis: a useful and conceptually unusual route to lactones and lactams S.V. Ley, L.R. Cox, G. Meek, Chem. Rev. 1996, 96, 423-442.
- Diastereoselective addition reactions of allylstannanes to carbonyl groups in the side-chain of π-allyltricarbonyliron lactone complexes S.V. Ley and L. Cox, J. Chem. Soc., Chem. Commun. 1996, 657-658.
- Synthesis of β-dimorphecolic acid exploiting highly stereoselective reduction of a side-chain carbonyl group in a π-allyltricarbonyliron lactone complex S.V. Ley, G. Meek, J. Chem. Soc. Perkin Trans. 1 1997, 1125-1134.
- 1,5-Asymmetric induction of chirality: highly diastereoselective addition reactions of organoaluminium reagents into ketone groups in the side-chain of π-allyltricarbonyliron lactone complex S.V. Ley, L.R. Cox, G. Meek, K.-H. Metten, C. Pique, J. Worrall, J. Chem. Soc., Perkin Trans. 11997, 3299-3314.
- 1,5 Asymmetric induction of chirality: highly diastereoselective synthesis of homoallylic tertiary alcohols by the Lewis acid-mediated addition of allylstannanes into ketones in the side-chain of π-allyltricarbonyliron lactone complexes L.R. Cox and S.V. Ley, J. Chem. Soc., Perkin Trans. 11997, 3315-3326.
- 1,5 Asymmetric induction of chirality: diastereoselective addition of organoaluminium reagents and allylstannanes to aldehyde groups in the side-chain of π-allyltricarbonyliron lactone complexes S.V. Ley, S. Burckhardt, L.R. Cox, G. Meek, J. Chem. Soc., Perkin Trans. 1 1997, 3327-3338.
- Highly diastereoselective synthesis of β-hydroxy carbonyl compounds using π-allyltricarbonyliron lactone complexes: a formal 1,7 asymmetric induction of chirality in a Mukaiyama Aldol reaction S.V. Ley and L.R. Cox, J. Chem. Soc., Chem. Commun. 1998, 227-228.
- A novel decomplexation of π-allyltricarbonyliron lactone complexes using borohydride reagents: a new route to stereodefined acyclic 1,5-diols and 1,5,7-triols S.V. Ley, S. Burckhardt, L.R. Cox and, J. M. Worrall, J. Chem. Soc., Chem. Commun., 1998, 229-230.
- Mukaiyama Aldol reactions of π-allyltricarbonyliron lactone and lactam complexes bearing trimethylsilyl enol ether side-chains: not just formal but genuine 1,7-induction of chirality S.V. Ley, L.R. Cox, B. Middleton, J.M. Worrall, J. Chem. Soc., Chem. Commun. 1998, 1339-1340.
- Tricarbonyliron complexes: an approach to acyclic stereocontrol L.R. Cox and S.V.Ley, J. Chem. Soc. Rev. 1998, 27, 301-314.
- A new route to functionalised π-allyltricarbonyliron lactam complexes from aziridines and their use in steroselective synthesis and oxidative conversion to β-lactams S.V. Ley and B. Middleton, J. Chem. Soc., Chem. Commun. 1998, 1995-1996.
- Double diastereodifferentiation in the Mukaiyama aldol reactions of π-allyltricarbonyliron lactone complexes; 1,7-vs 1,2-asymmetric induction S.V. Ley, L.R. Cox, J.M. Worrall, J. Chem. Soc., Perkin Trans. 1 1998, 3349-3354.
- New building blocks for efficient and highly diastereoselective polyol production: synthesis and utility of (R,R,S,S)-and (S,S,R,R,)-2,3-butane diacetal protected butane tetrol derivatives J. Barlow, D.J. Dixon, A.C. Foster, S.V. Ley, D.R. Reynolds, J. Chem. Soc., Perkin Trans. 1 1999, 1627-1630.
- Total synthesis of the cholesterol biosynthesis synthase inhibitor 1233A via a π-Allyltricarbonyliron Lactone Complex S.V. Ley, R.W. Bates, E. Fernández-Megía, S.V. Ley, K. Rück-Braun, D.M.G. Tilbrook, J. Chem. Soc., Perkin Trans. 1 1999, 1917-1926.
- Reductive Decomplexation of p-Allyltricarbonyliron Lactone Complexes: A New Route to Stereodefined Acyclic 1,5-Diols and 1,5,7-Triols S.V. Ley, S. Burckhardt, L.R. Cox and J.M. Worrall, J. Chem. Soc., Perkin Trans. 1, 2000, 211.
- 1,7- Asymmetric Induction of Chirality in a Mukaiyama Aldol Reaction using p-Allyltricarbonyliron Lactone Complexes: Highly Diastereoselective Synthesis of α-Substituted β-Hydroxy Carbonyl Compounds S.V. Ley and E.A. Wright, J. Chem. Soc., Perkin Trans. 1, 2000, 1677.
- The Use of π-Allyltricarbonyliron Lactone Complexes in the Synthesis of the Resorcylic Macrolides α- and β- Zearalenol S.V. Ley and S. Burckhardt, J. Chem. Soc., Perkin Trans. 1, 2000, 3028.
- The Use of π-Allyltricarbonyliron Lactone Complexes in the Synthesis of the Resorcyclic Macrolides and Zearalenol S. Burckhardt and S.V. Ley, J. Chem. Soc., Perkin Trans. 1, 2002, 874.
- Synthesis of Taurospongin A: A Potent Inhibitor of DNA Polymerase and HIV Reverse Transcriptase using p-Allyltricarbonyliron Lactone Complexes C.J. Hollowood, S.V. Ley and S.Yamanoi, J. Chem. Soc., Chem. Commun., 2002, 1624.
- Reductive Decomplexation of p-Allyltricarbonyliron Lactone Complexes: A New Route to Stereo-defined 1,7-Diols and 2,3-Diene-1,7-diols S.V. Ley and C.J. Hollowood, J. Chem. Soc., Chem. Commun., 2002, 2130.
- Use of π-Allyltricarbonyliron Lactone Complexes in the Synthesis of Taurospongin A: A Potent Inhibitor of DNA Polymerase β and HIV Reverse Transcriptase C.J. Hollowood, S.V. Ley and S. Yamanoi, Org. Biomol. Chem., 2003, 1, 1664.
- Reductive Decomplexation of π-Allyltricarbonyliron Lactone Complexes using Sodium Naphthalenide as a Route to Stereodefined 1,7-diols and 2,3-diene-1,7-diols C.J. Hollowood and S.V. Ley, Org. Biomol. Chem., 2003, 1, 3197.
- 1,5-Asymmetric Induction of Chirality using π-Allyltricarbonyliron Lactone Complexes: Highly Diastereoselective Synthesis of α-Functionalised Carbonyl Compounds C.J. Hollowood, S.V. Ley, and E.A. Wright, Org. Biomol. Chem., 2003, 1, 3208.
- Synthesis of (-)-Gloeosporone, a Fungal Autoinhibitor of Spore Germination using a π-Allyltricarbonyliron Lactone Complex as a Templating Architecture for 1,7-Diol Construction E. Cleator, J. Harter, C.J. Hollowood and S.V. Ley, Org. Biomol. Chem., 2003, 1, 3263.