The enantioenriched SIA heterocycles can be further modified via late-stage functionalization or can be cyclized to give novel tricyclic chemical scaffolds. Aryl bromide 25 was coupled to either PMP boronic acid or vinyl boronic acid in a Suzuki reaction to provide 33 and 34. The aryl bromide was also functionalized in a Sonogashira reaction producing compounds 35 and 36. These transformations demonstrate the late-stage manipulations of an enantioenriched SIA. The free alcohol in compound 26 and 27 functions as a synthetic handle for building a novel classes of tricyclic SIAs. Acetoxylation of the alcohol followed by an intramolecular palladium-catalyzed cyclization forges a new C-C bond generating tricycle 36. Alternatively, compound 26 readily undergoes an intramolecular SNAr reaction to furnish the 8-membered tricyclic ether 37. Conversion of the allylic alcohol of 27 to the allylic sulfonamide led to a facile SNAr reaction yielding compound 38. The enantioenriched heterocyclic SIAs can be functionalized readily using palladium-catalyzed cross coupling reactions, or cyclized to yield carbon, oxygen, or nitrogen tricyclic SIAs.