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As a consequence of nature鈥檚 鈥渃ombinatorial鈥� approach to the evolution of secondary metabolites, natural products are often isolated as members of families of closely related structures. For the purposes of learning about the potential utility of such families of bioactive natural products, a synthesis design that is amenable to many family members and unnatural analogues is particularly attractive. In that light, I will discuss some of our recent efforts to develop general approaches to natural product families among the chlorosulfolipids, polyhalogenated monoterpenoids, lissoclimide diterpenoids, and isocyanoterpenes.