Equilenin

Chemistry

Synthesis

Total synthesis

The synthesis developed by the Bachmann group started from Butenand's ketone – and which can be readily prepared from 1,6-Cleve's acid. The approach was based on well-established transformations like the Claisen condensation, the Reformatsky reaction, the Arndt–Eistert reaction, and the Dieckmann condensation. in this synthesis, a mixture of stereoisomers were prepared and then resolved, and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.

The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.

References

References

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