Model Studies Towards the Total Synthesis of the Anticancer Agent Roseophili­n

E. M. E. Viseux; P. J. Parsons; J. B. J. Pavey; C. M. Carter; I. Pinto

doi:10.1055/s-2003-41498

LETTER

Model Studies Towards the Total Synthesis of the Anticancer Agent Roseophilin

E. M. E. Viseux^a, P. J. Parsons*^a, J. B. J. Pavey^b, C. M. Carter^a, I. Pinto^c
^a The Chemical Laboratories, School of Chemistry, Physics & Environmental Science, University of Sussex, Falmer, Brighton, East Sussex BN1 9QJ, UK
e-Mail: P.J.Parsons@sussex.ac.uk;
^b AstraZeneca R&D Charnwood, Process R&D, Bakewell Road, Loughborough, Leics LE11 5RH, UK
^c Medicinal Chemistry, GlaxoSmithKline, New Frontiers Science Park (North), Harlow, Essex CM19 5AW, UK

Abstract

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Abstract

In our new approach to the anticancer agent roseophilin (1), a concise, stereocontrolled synthesis of the bicyclic model system 16 was achieved. Key steps include a diastereoselective Ireland-Claisen rearrangement and a stereoselective construction of the hexahydro-cyclopenta[b]pyrrol-6-one core via a tandem intramolecular aza-Wittig/[3+2]-cycloaddition sequence.

Key words

[5] roseophilin - azomethine ylid - dipolar cycloaddition - aza-Wittig - Ireland-Claisen rearrangement

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References

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NOE studies of compound 16 (Figure [3] ).

Figure 3

Model Studies Towards the Total Synthesis of the Anticancer Agent Roseophili­n

Model Studies Towards the Total Synthesis of the Anticancer Agent Roseophilin