With a robust route to the dienoate (10-7) and the keto-lactone (11-5) already established (cf. Scheme 12B and Scheme 11B, respectively), we turned to synthesizing the enoxysilane (10-8) and pursuing the fragment coupling (Scheme 13B). The enoxysilane fragment (10-8) was prepared by formation of the triethylsilyl enol ether of 11-5. Treatment of 10-8 and dienoate 10-7 with catalytic BF3•OEt2 initiated a Mukaiyama-aldol reaction, which resulted in an intermediate alcohol. Treatment of the intermediate aldol product with Burgess reagent formed coupling product 13-1 in 67% yield over the two steps. Condensation of hydroxylamine onto the ketone functionality led to an aza-triene intermediate, which underwent a 6π-electrocyclization and loss of water to form C3-deoxy-xylogranatin F (10-1) in excellent yield (92%). A selective benzylic oxidation of 10-1 at position A, which would be analogous to the benzylic oxidation described in the synthesis of xylogranatopyridine B (1-1), was planned to furnish C3-keto-xylogranatin F (13-2).