Structure elucidation and synthesis of (4S,5S,6Z,8E )-5-hydroxydeca-6,8-dien-4-olide [(S,S)-sapinofuranone B]—a novel γ-lactone metabolite of Acremonium strictum

Enantiocontrolled Synthesis of 3‐Pyrrolines from α‐Amino Allenes

“…[13] Substitution of the remaining unprotected hydroxy group, [14] followed by base-induced elimination, [15] afforded the desired propargylic alcohol (R)-1f. Treatment of allenyl amide 3a with 4.5 equiv.…”

“…1 H NMR (400 or 300 MHz) and 13 6 ]DMSO (δ ϭ 2.50 ppm for 1 H and 39.51 ppm for 13 C) as internal standards. For the determination of optical purity we used a Varian 3800 analytical GC fitted with a CP-Chirasil-Dex CB column for compound 1d and 4cЈ and a Waters 2690 analytical HPLC with OD-H column for compounds 4c, 4d and 4f.…”

“…[11] Distillation (85Ϫ94°C, 0.20 mbar) afforded the 1,3-dioxolane in 97% yield (49.47 g, 0.201 mol). Reduction with LiAlH 4 [12] and subsequent mono-benzylation, [13] followed by substitution of the remaining unprotected alcohol [14] and elimination, [15] afforded (R)-1f in 36% 3242 overall yield. The characterization of the title compound has been published before.…”

DIBAL-Mediated Reductive Transformation of trans-Dimethyl Tartrate Acetonide into ε-Hydroxy α,β-Unsaturated Ester and Its Derivatives

“…This product spectroscopically matched that of the known compound. xxv ; [α] D 20 = −24.7 ( c 2.60, CHCl 3 ), [lit. xxvi [α] D 23 = −24.1 ( c 2.6, CHCl 3 )]; 1 H NMR (300 MHz, CDCl 3 ) δ 4.10 (q, J = 7.2 Hz, 2H), 3.86 (dt = 7.5, 3.6 Hz, 1H), 3.74 (m, 2H), 3.62 (m, 1H), 2.53−2.36 (m, 3H), 1.92 (m, 1H), 1.81 (m, 1H), 1.36 (s, 3H), 1.35 (s, 3H), 1.22 (t, J = 7.2 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 173.2, 108.8, 81.0, 76.1, 61.8, 60.5, 30.6, 27.9, 27.2, 26.9, 14.1.…”

Diplofuranones A and B, two further new 4-monosubstituted 2(3H)-dihydrofuranones produced by Diplodia corticola, a fungus pathogen of cork oak

“…20 Butanolides are rare as naturally occurring compounds but are closely related to butenolides, which are well known as plant, fungal and lichen metabolites that also exhibit interesting biological activity. 21 Among these there are the seiridins, which are 3,4-dialkylbutenolides isolated from the culture filtrates of three species of Seiridium associated with the canker diseases of cypress.…”