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I have been involved in designing synthetic routes to naturally occurring strained architectures, such as ladderanes, characterized by multiple concatenated cyclobutane rings. In addition to the first catalytic enantioselective synthesis of (–)-car-3-ene-2,5-dione, we have applied the organocatalytic alkylative desymmetrization, developed in our lab, to a symmetry inspired unified strategy for the enantioselective synthesis of both (+)-[3]-ladderanol and (–)-[5]-ladderanoic acid. To uncover the rationale behind nature’s selection of these architectuarally unique natural products, we have synthesized structurally related unnatural ladderanes. Apart from synthesizing ladderane-based natural products, we have designed and synthesized unnatural benzo-[3]-ladderanol in an enantioselective fashion in our effort to devise natural product (NP)-based discovery. To accomplish this synthesis, we have introduced the concept of alkoxy-directed dienamine catalysis in an effort to overcome the shortcomings of classical dienamine catalysis.

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