Model Studies Towards the Total Synthesis of the Anticancer Agent Roseophili­n

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

References

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The use of LHMDS seems to favour the E-enolate and the addition of triethylamine to the trimethylsilyl chloride enhances its reactivity.

26

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

Figure 3