616207-71-7

Upstream product

• 637029-39-1 (4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-isopropyl-5-methyl-tetrahydro-pyran-2-one 
• 93215-51-1 1-tert-butoxy-1-(trimethylsiloxy)ethylene 
• 116660-67-4 (2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 53045-65-1 2,4-dimethylhex-5-en-3-ol 
• 1030599-26-8 (3R,4R,5R)-4,6-dimethylheptane-1,3,5-triol 
• 643755-75-3 (4R,6R)-4-Hydroxy-6-isopropyl-5-methylene-tetrahydro-pyran-2-one 
• 795279-40-2 (2R,3R)-2-(5-methoxycyclohexa-1,4-dienyl)-4-methylpentan-2-ol 
• 795279-41-3 (4S,5R)-5-hydroxy-4,6-dimethyl-3-oxoheptanoic acid methyl ester 
• 224580-63-6 tert-Butyl (3SR,4S,5R)-5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-4,6-dimethylheptanoate 
• 171075-74-4 (2R)-1-(benzyloxy)hex-4-yn-2-ol 
• 115560-90-2 (2R)-(E)-1-(phenylmethoxy)-4-hexen-2-ol 
• 850353-28-5 (4R,5S,6R)-6-Isopropyl-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-one 
• 760978-00-5 (3R,4S,5R)-5-Benzyloxy-3-hydroxy-4,6-dimethyl-heptanoic acid methyl ester 
• 538350-24-2 ((4R,5S,6R)-6-Isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Total syntheses of Prelactone V and Prelactone B

The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from D-glucose. The synthesis involves isopropylidene acetal formation of D-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.

Anti-Aldol reactions of chiral alcohol-substituted vinylogous urethanes and the synthesis of (-)-prelactone B

This paper describes a convenient and efficient method for synthesizing chiral alcohol-substituted vinylogous urethanes, in which the double bond has E configuration was determined by single crystal X-ray analysis. In addition, we investigated the anti-aldol reactions of these chiral vinylogous urethane anions. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2, 1]-heptan-2-ol as a chiral auxiliary, provided the best enantioselectivities, and the resulting vinylogous urethane lactone could be used for the synthesis of (-)-prelactone B. A plausible mechanism for the generation of major enantiomeric isomer was discussed.

Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters

A versatile methodology for the asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters has been developed that relies on a series of Evans' aldol, hydroxyl-directed cyclopropanation, methanolysis, and Hg(II) mediated cyclopropane ring-opening reactions for stereocontrol.

Total asymmetric syntheses of β-hydroxy-δ-lactones via umpolung with sulfur dioxide

Cyclic stereotriads and stereotetrads of the β-hydroxy-d-lactone type, e.g. prelactonesBandE, commonin polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy) penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-d-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The d-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3- dienes.

Application of silacyclic allylsilanes to the synthesis of β-hydroxy-δ-lactones: synthesis of Prelactone B

Silacyclic allylsilanes generated through a silene-diene Diels-Alder cycloaddition represent versatile bifunctional reagents for organic synthesis. This is demonstrated in a short stereocontrolled synthesis of (±)-Prelactone B.

First concise total synthesis of 5-epi-prelactone B

First short total synthesis of 5-epi-prelactone B has been achieved involving Sharpless asymmetric epoxidation and intramolecular hydride transfer reaction for formation of the aldol product by nonaldol chemistry as the key steps. Copyright Taylor & Francis Group, LLC.

Silenes in organic synthesis: A short synthesis of prelactone B

The development of a synthetic methodology for the generation of silacyclohexenes through the cycloaddition of silenes with dienes and their subsequent elaboration to δ-lactones was discussed. It was found that the allyl silane component of the silacycloh

A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: Synthesis of (+)-prelactones B, C and V

Reactions of homoallylic alcohols with aldehydes in the presence of acid catalysts gave multisubstituted tetrahydropyrans with the creation of one to three new stereogenic centres in a single-pot process. The utility of this approach is extended to the en

An asymmetric synthesis of (-)-prelactone B

An efficient synthesis of (-)-prelactone B has been developed using 1,2-cyclohexylidene glyceraldehyde as the chiral template. The key features of the synthesis were stereoselective crotylation of 1,2-cyclohexylidene glyceraldehyde and enantioselective re

Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B

Catalytic and stoichiometric asymmetric sulfur ylide reactions were employed to prepare alkyl-aryl epoxide intermediates in a convergent manner. These epoxides were utilized in efficient syntheses of the mevinic acid analogue 1 and prelactone B. Graphical abstract.