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Differential synthetic access to an advanced C26-C40 northern hemisphere fragment of spirastrellolide B and to a related [5,5,7]-bis-spiroketal analogue from a common intermediate has been achieved. Central to this venture is the regiocontrolled functionalization of a C(31-32) alkyne, exploiting different transition metal catalysts (cf. Pt(II) and Au(I)).

Spirastrellolide B: Construction of the C(26)–C(40) Northern Hemisphere and a Related [5,5,7]-Bis-spiroketal Analogue