The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment.


The convergent synthesis of the C1-C15 AB-spiroacetal subunit I of altohyrtin A/spongistatin 1 is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral Me ketones, under Ipc2BCl mediation, to establish the C5, C9 and C11 stereocenters, and formation of the desired thermodn. spiroacetal under acidic conditions. The scalable synthetic sequence developed provided access to multi-gram quantities of I, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin, as reported in Part 4.

Organic & Biomolecular Chemistry