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Herein, we report the expansion of chemical space available from chitin, accessible via the biogenic <i>N</i>-platforms 3A5AF, M4A2C, and di-HAF. The biologically active heteroaromatics furo[3,2-<i>d</i>]pyrimidin-4-one and furo[3,2-<i>d</i>]pyrimidin-4-amine can be selectively accessed from 3A5AF and M4A2C, respectively. The chiral pool synthon di-HAF is a viable substrate for Achmatowicz rearrangement, providing streamlined access to 2-aminosugars possessing a versatile hydroxymethyl group at C5.