The case studies depicted above only scratch the surface of what is possible using dDCC as applied to complex natural product synthesis. Figure illustrates further the power of dDCC for another 6 natural product syntheses using unique carboxylic acid building blocks. cis-Solamin was isolated from the roots of Annona muricata and is a potent cytotoxic compound that inhibits the mitochondrial respiratory enzyme complex I (NADH ubiquinone oxidoreductase). Intermediate 52 is a well-established precursor for cis-Solamin and has been prepared three times in 7-15 steps (33-57% ideality) based on conventional 2e -synthetic with extensive use of olefin functionalization and phosphonium ylide chemistry. The radical approach described herein uses one of the most abundant chiral building blocks available, tartaric acid. Thus, sequential dDCC couplings (proceeding in 60% and 43% yield with perfect diastereocontrol) between readily available 48 with simple acids 49 and 50 enabled the rapid assembly of the main chain, followed by a simple stereocontrolled dihydroxylation/cyclization and deprotection to afford 52 in 6 steps (50% ideality). Aphanorphine (57), isolated from the freshwater blue-green algae named aphanizomenon flos-aquae, Drawing inspiration from Ley's pioneering studies on dioxane-based chiral auxiliaries, 42 the morpholino-acid RAE 63 was designed as a precursor to the 1,2-aminoalcohol motif (synthesized in 3 steps, see SI) and employed in the synthesis of two unrelated amine-containing natural products. The first of these was SF2768 (67), a unique alkaloid containing an isonitrile functionality, with biological relevance in the area of bacterial copper homeostasis. The key hydroxylysine unit 65 was previously constructed by lengthy functional group manipulations of a chiral building block with poor stereocontrol (1:1). By using a stereocontrolled dDCC approach commencing from 63 and glutamate 64, this key fragment 65 can be accessed in a single step (42% yield, >20:1 dr) followed by exchange of the Cbz to Boc group to complete the formal synthesis in steps. The second natural product prepared from 63, complanine (71), is an amphipathic substance isolated from the marine fireworm, Eurythoe complanata. The prior synthesis was accomplished via homologation of an alkyne followed by the construction of amino alcohol motif by using enantioselective nitrosoaldol reaction. Stereoselective dDCC between 63 and RAE 68 (40% yield, >20:1 dr) followed by Cbz deprotection afforded chiral amino alcohol 70 in 5 steps.