765940-99-6

Upstream product

• 765940-97-4 (R)-(+)-1-phenylbut-3-enyl acrylate 
• 114996-00-8 1-<(trimethylsilyl)oxy>-1-ethoxy-1,3-butadiene 
• 100-52-7 benzaldehyde 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 
• 181227-42-9 (+)-(R)-1-phenylbut-3-en-1-yl acetate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 1004960-84-2 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 72853-47-5 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 46117-36-6 but-3-enoic acid phenyl ester 
• 1178586-81-6 C₁₈H₁₈O₃ 
• 1178586-65-6 C₁₈H₁₈O₃ 
• 86170-45-8 benzyl 3-butenoate 

Downstream Products

• 765941-01-3 (3S,4S,6R)-3,4-dihydroxy-6-phenyltetrahydropyran-2-one 
• 112607-33-7 (+)-(R)-δ-(phenyl)-δ-valerolactone 

Relevant academic research and scientific papers

Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones via Chemoenzymatic Sequential DKR-RCM Reaction

The enantiomerically pure 5,6-dihydropyran-2-ones play a crucial role as the building blocks in the synthesis of various bioactive compounds. A new straightforward protocol toward enantiomerically pure 5,6-dihydropyran-2-ones based on enzymatic dynamic ki

Asymmetric Synthesis of α,β-Unsaturated δ-Lactones through Copper(I)-Catalyzed Direct Vinylogous Aldol Reaction

A simple methodology for the asymmetric synthesis of chiral α,β-unsaturated δ-lactones was achieved by copper(I)-catalyzed direct vinylogous aldol reaction (DVAR) of β,γ-unsaturated esters and various aldehydes, including aromatic aldehydes, heteroaromatic aldehydes, α,β-unsaturated aldehydes, and aliphatic aldehydes. For aromatic and heteroaromatic aldehydes, a one-pot reaction consisting of DVAR, isomerization of the unsaturated carbon-carbon double bond from (E)-form to (Z)-form, and subsequent intramolecular transesterification was required to get the lactones in moderate to high yields with high enantioselectivity. For α,β-unsaturated and aliphatic aldehydes, the DVAR proceeded directly to afford the lactones in moderate yields with high enantioselectivity. In the DVAR, various functional groups were well tolerated. Moreover, the methodology was nicely applicable to the aldehyde group distributed in natural products, derivatives of natural product, and derivatives of drug molecules (atomoxetine and naproxen). The mechanism studies revealed that α-addition was reversible and not favored, which accounted for the excellent regioselectivity in the DVAR. The copper(I)-dienolate species generated through deprotonation was proposed to form an equilibrium with an allylcopper(I) species, which reacted with aldehydes to afford the DVAR products through a catalytic asymmetric allylation of aldehydes. Finally, the robustness of the present reaction was demonstrated by a gram-scale reaction, and the utility of the present methodology was showcased by the formal asymmetric synthesis of ezetimibe and fostriecin.

Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

A novel synthetic route to optically active saturated and unsaturated δ-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate s

Dynamic kinetic resolution of homoallylic alcohols: Application to the synthesis of enantiomerically pure 5,6-dihydropyran-2-ones and δ-lactones

Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transfor

The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport

An in vivo nuclear export assay (immunostaining of Rio2 in HeLa cells) demonstrated that (R)-goniothalamin is an inhibitor of nucleocytoplasmic transport above 500 nM, which was rationalized also by molecular modeling. The cytotoxic styryl lactone natural product was prepared via an enantioselective Cr(III) catalyzed hetero Diels-Alder reaction and a Sonogashira coupling. A series of analogs was synthesized and only the oxidized goniothalamin derivative featuring an alkyne spacer was found active. Unsaturated lactones of natural origin other than leptomycin (LMB) are thus suggested to operate via a similar mechanism targeting the CRM1 nuclear receptor.

Simple and fast synthesis of new axially chiral bipyridine N, N'-dioxides for highly enantioselective allylation of aldehydes

Unsymmetrically 3,3'-substituted axially chiral bis(tetrahydroisoquinoline) N,N'-dioxides can be prepared in just three steps. They exhibit unique catalytic activity (turnover frequency, enantioselectivity, substrate scope) in the asymmetric allylation of

A stereoselective approach to 1,3-amino alcohols protected as cyclic carbamates: Kinetic vs. thermodynamic control

Direct enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition)

α,β-unsaturated δ-lactones from copper-catalyzed asymmetric vinylogous mukaiyama reactions of aldehydes: Scope and mechanistic insights

A direct regio-, diastereo-, and enantiocontrolled access to α,β-unsaturated δ-lactones is described, based on the reaction of a silyl dienolate and an aldehyde in the presence of 10% of Carreira's catalyst. The scope and limitations of this reaction, as well as mechanistic insights concerning the reactivity of an allyl copper species, are discussed.

Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C 1-C8 and C15-C21 subunits of (+)-discodermolide

Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective α-deoxygenation provides 1,3-trans-β-hydroxy-6- lactones stereoselectively. This protocol has been applied for the synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide.