Efficient distal-difunctionalization of cavitand bowls.
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Crystallography, X-Ray↗
Biomedical subjects
M S Sherburn
Publications and source records attributed to M S Sherburn.
Stereocontrol of intramolecular Diels-Alder reactions: synthetic studies and transition structure modeling with c5-substituted 1,3,8-nonatrienes and nonadienynes.
An investigation into the endo/exo selectivity and pi-diastereofacial selectivity of ester-tethered intramolecular Diels-Alder reactions is reported. High levels of exo selectivity are realized with terminally substituted dienophiles, and high lk pi-diastereofacial selectivities are induced by the presence of a bulky dioxolanyl substituent at the allylic position of the tether. Precursors 19S, 20S, and 21S, readily prepared from glucose, provide densely functionalized bicyclic lactones of predictable stereochemistry in high yields in enantiomerically pure form upon thermolysis at 110 degrees C. B3LYP/6-31G(d) theory provides good descriptions of transition structures for these reactions and allows an understanding of the formation of the major cycloadducts.
Journal Article↗
Monolithiocavitands: versatile intermediates for new cavitand-based hosts.
[figure: see text] Cavitand bowls carrying two derivatizable groups at the rim have been efficiently prepared through a selective lithium/halogen exchange-electrophile quenching procedure. This methodology lends itself to the single-step preparation of the first all carbon-linked bis-bowl and a new class of inherently chiral cavitands.
Journal Article↗
Conjugated triene oxidation products of alpha-farnesene induce symptoms of superficial scald on stored apples.
The sesquiterpene alpha-farnesene (1) and its conjugated triene oxidation products accumulate in the skin of apples after harvest and are implicated as the causal agents of superficial scald. Conjugated triene oxidation products and analogues were synthesized and applied to the surface of Granny Smith apples either as vapors or in squalane. Farnesyl hydroperoxide (2a), trienol (2b), endoperoxide (3a), dehydronerolidol (5), and cumyl hydroperoxide (4) all produced the symptoms of superficial scald when applied at nanomolar doses. Scald-inducing activity was dependent on the mode of application. Farnesyl hydroperoxide (2a) was the most active conjugated triene when applied directly to the apple skin. Trienol (2b) also induced scald symptoms and partially reversed the inhibition of scald caused by diphenylamine.
Food Handling↗