A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin

Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide

“…Removal of the chiral auxiliary by LiBH 4 and manipulation of protecting groups in five steps gave the alcohol 14 via 13 . After Parikh–Doering oxidation of 14 , the aldehyde generated was reacted with Horner–Wadsworth–Emmons reagent 16 [ 8 ] to yield 15 , which on hydrogenation followed by addition of a methyl group produced 17 . After removal of the auxiliary by LiBH 4 , an ethyl ketone function was constructed (compound 18 ), and the exo -methylene function was introduced by Peterson olefination, followed by basic treatment, whereas other methods, such as the Wittig and Petasis reactions did not produce the desired compound, probably due to the low reactivity of the ethylketone moiety.…”

Chemical Syntheses and Chemical Biology of Carboxyl Polyether Ionophores: Recent Highlights

“…We have tried to extract the strategic disconnections toward the carbon skeletons and key methods involved in the construction of the structural subunits, rather than comprehensively detailing every synthetic step from all the different approaches. A compilation of synthetic studies on other carboxyl polyether ionophore natural products completed in the time period from 2001 to 2018 is given in Table S1 (Supporting Information) with key transformations highlighted …”

Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes

“…Alcohol 21 was oxidized to the corresponding aldehyde 22 which reacted with phosphonate 23 [24], to afford triene 24 with the E-configuration across the newly created double bond (Scheme 6). This triene was subjected to the cyclization induced by Me 2 AlCl; no reaction was, however, noticed.…”