ABSTRACT: An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads has been developed. Either 2-butyne or propyne is subjected to rhodium-catalyzed silylformylation and in situ crotylation of the resulting aldehydes. Tamao oxidation under either “standard ” conditions or “aprotic ” conditions then delivers the completed stereotriads in a three-step, two-pot sequence. In contrast to the classical Roche ester approach, the α-stereocenter is obtained for “free.” Since its full development by Roush almost 30 years ago,1the “Roche ester ” approach to the construction of stereotriad building blocks for nonaromatic polyketide natural products synthesis has emerged as, and remains, one of the most widely ...
It has been hypothesized that the polypropionates isolated from Siphonaria zelandica, siphonarin B, ...
Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselec...
Polypropionates represent a large family of natural products and several strategies have been develo...
An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads...
The polypropionate motif is ubiquitous, being characteristic of the most important family of natural...
Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allyli...
Linear carbon-carbon chains with alternating hydroxyl and methyl substituents are a common motif in ...
Aromatic polyketides are generated in a divergent fashion from linear polyketide chains. These seemi...
Various propargyl alcohols were synthesized via Grignard reactions. These alkynic alcohols are tethe...
The sequential aldol reactions of thiopyran derivatives 112 and 119 to rapidly generate hexapropiona...
Herein, a major breakthrough in a sulfur dioxide-mediated oxyallylation cascade reaction is reported...
The Matteson homologation was found to be a versatile tool for the construction of the linear polyke...
An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious a...
Abstract: Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)-or (1's...
Silylcarbinols generated from the 1,2-addition of dimethyl(phenyl)silyllithium to cyclic $\alpha,\be...
It has been hypothesized that the polypropionates isolated from Siphonaria zelandica, siphonarin B, ...
Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselec...
Polypropionates represent a large family of natural products and several strategies have been develo...
An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads...
The polypropionate motif is ubiquitous, being characteristic of the most important family of natural...
Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allyli...
Linear carbon-carbon chains with alternating hydroxyl and methyl substituents are a common motif in ...
Aromatic polyketides are generated in a divergent fashion from linear polyketide chains. These seemi...
Various propargyl alcohols were synthesized via Grignard reactions. These alkynic alcohols are tethe...
The sequential aldol reactions of thiopyran derivatives 112 and 119 to rapidly generate hexapropiona...
Herein, a major breakthrough in a sulfur dioxide-mediated oxyallylation cascade reaction is reported...
The Matteson homologation was found to be a versatile tool for the construction of the linear polyke...
An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious a...
Abstract: Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)-or (1's...
Silylcarbinols generated from the 1,2-addition of dimethyl(phenyl)silyllithium to cyclic $\alpha,\be...
It has been hypothesized that the polypropionates isolated from Siphonaria zelandica, siphonarin B, ...
Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselec...
Polypropionates represent a large family of natural products and several strategies have been develo...