Synthesis and stereochemistry of decarestrictines H and J

Add time:08/08/2019    Source:sciencedirect.com

The first synthesis of (7S,9R)-decarestrictine H and (7R,9R)-decarestrictine H as well as the improved synthesis of decarestrictine J were achieved. The overall yields of (7S,9R)-decarestrictines H and J were 20.9% each in nine to ten steps from (R)-Roche ester using a unified synthetic route via esterification with 3,3-ethylenedioxyhex-5-enoic acid and ring-closing metathesis, which were the key steps. The relative stereochemistry of decarestrictine H was determined to be 7,9-syn by comparing the spectral data of the natural product and synthetic epimers of decarestrictines H.

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