Mild basic hydrolysis of cyclobuxine triacetate led to N,N'-diacetate (Ib), and strong basic hydrolysis gave N-monoacetate (IC) in quantitative yield. The remaining N-acetyl group required vigorous acid conditions for removal. The monoacetate, upon oxidation, yielded a ketone that rapidly lost methylamine in base to form a material with spectral characteristics of the cyclopentenone mixture from earlier structural investigations, indicating 20-N-acetyl group hydrolysis assisted by cis-interaction with the 16α-hydroxyl group. Treatment under strong basic conditions recovered 60% of 16-dehydrocyclobuxine N,N'-diacetate, supporting assignment of α-configuration to the 20-methylamino group consistent with biogenetic precedent. Penicillium chrysogenum grown on a simple medium produced small amounts of solvent-extractable penicillins along with 6-aminopenicillanic acid (6-APA) and another low-activity β-lactam compound. A new compound (II) was isolated via activated carbon adsorption, elution, and potato starch chromatography. It was chromatographically homogeneous, indistinguishable from penicillin N in chromatographic systems, showed penicillinase-hydroxylamine assay activity (~1,200 p/mg), low antibacterial activity against Staphylococcus aureus (209P) comparable to penicillin N, acid and penicillinase lability similar to penicillin N, and gave a ninhydrin-reactive spot coinciding with antibiotic activity. Treatment with mercuric chloride yielded a mercaptide, and hydrolysis gave L-α-aminoadipic acid (deduced from comparison with D-α-aminoadipic acid via chromatography, IR, XRD, and opposite optical rotatory dispersion). The compound, named isopenicillin N, has structure II differing from penicillin N only in C6' configuration, suggesting possible biosynthetic pathway convergence between Penicillium and Cephalosporium species with aminoadipyl side chain stereochemistry as a differentiating factor. Oxidative coupling of trans,trans-4,10-tetradecadiene-1,7,13-triyne with cupric acetate in pyridine and subsequent potassium t-butoxide treatment yielded two products: a major monodehydro[14]annulene (I) with 4 cis and 2 trans double bonds, and a minor product identified as 1,8-bisdehydro[14]annulene (II), an unusual aromatic compound. II's deuteriochloroform NMR spectrum shows three multiplets at 15.54, 1.57, and 0.45 τ (relative intensities 2:4:4), indicating symmetry and 10 protons. The 15.54 τ triplet (J=13.3 c./s.) is assigned to shielded HO protons, the 0.45 τ double doublet (J=13.3, 8.0 c./s.) to Hb/Hb', and the 1.57 τ doublet (J=8.0 c./s.) to Ha/Ha', suggesting cis- and trans-interactions. Elemental analysis (C, 93.94; H, 6.02) supports C14H10 (calcd.: C, 94.34; H, 5.66) over C14H12.