Olefin cross metathesis based de novo synthesis of a partially protected L-amicetose and a fully protected L-cinerulose derivative

Abstract

SummaryCross metathesis of a lactate derived allylic alcohol and acrolein is the entry point to a de novo synthesis of 4-benzoate protected L-amicetose and a cinerulose derivative protected at C5 and C1.

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…Classification is according to the "expendable" alkene using in the cross metathesis process. Several papers report on the cross metathesis of inexpensive low molecular weight α,β-unsaturated carbonyl compounds with other more precious alkenes, including cross metatheses of: (1) acrolein with a 22-carbon α,ω-diene derivative for preparation of miyakosyne A and stereoisomers [440], with allylic alcohols for six-membered ring carbohydrate syntheses [441], and with an allylpiperidine derivative (e.g. 135) for total synthesis of himeradine A [442]; (2) methacrolein with an alkene spiroacetal for total synthesis of bistramide A [443]; (3) methyl vinyl ketone with allylic alcohols as part of a general arylamine synthesis route [444]; (4) various enones, acrylates, and allylic alcohols with 4-pentylpyranones [445]; (5) various acrylate esters with undeca-1,9-dien-6-ol derivatives (e.g.…”

Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis

“…We first investigated conditions for the RCM of 1t and found that, compared to the standard conditions, a fivefold increased amount of second generation Grubbs catalyst A is required for quantitative conversion. Our recent positive experiences 22,44 with the Umicore M51 catalyst (B) 45 prompted us to test this Ru-alkylidene in the RCM of 1t. Gratifyingly, full conversion of 1t to 10 was accomplished with a notably reduced catalyst loading of 2.5 mol% under otherwise identical conditions.…”

Cross‐metathesis of fatty acid methyl esters with acrolein: An entry to a variety of bifunctional compounds

“…Therefore, cross‐metathesis of FAMEs with acrolein could in principle lead to fully bio‐sourced compounds. A literature survey showed that acrolein has been rarely used in cross‐metathesis reactions probably because of its lower reactivity as compared to other acrylic derivatives . Herein, we present a thorough study of the cross‐metathesis of several FAMEs with acrolein.…”