36170-05-5

Upstream product

• 725225-82-1 (5R)-5-(dec-9-enyl)-3-[(4S)-(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]dihydrofuran-2(3H)-one 
• 725225-81-0 Imidazole-1-carbothioic acid O-[(S)-((R)-5-dec-9-enyl-2-oxo-tetrahydro-furan-3-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl] ester 
• 150782-93-7 (3R,4R)-1-diazo-3,4-epoxy-14-(2-tetrahydropyranyloxy)tetradecan-2-one 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 53463-68-6 1-bromo-10-decanol 
• 112-47-0 1,10-Decanediol 
• 1312136-34-7 (R)-4-benzyl-3-(3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-propanoyl)oxazolidin-2-one 
• 106673-33-0 8-benzyloxy-1-octanal 
• 31600-54-1 8-(benzyloxy)octan-1-ol 
• 629-41-4 1,8-Octanediol 

Relevant academic research and scientific papers

Rubrenolide, total synthesis and assignment of its absolute configuration

The total synthesis of rubrenolide 1, a naturally occuring γ-lactone, is described. The γ-lactone was prepared by using the photo-induced rearrangement of an epoxy diazomethyl ketone as the key step. The diol side chain was introduced by a condensation with isopropylidene glyceraldehyde. During the synthesis it was concluded that the stereochemistry of the secondary alcohol was orinally incorrectly assigned. Rubrenolide has the 4R, 2S, 2′R-configuration.

Stereoselective total synthesis of rubrenolide and rubrynolide

The stereoselective total synthesis of rubrenolide and rubrynolide has been accomplished successfully. The synthetic strategy involves Evans alkylation and asymmetric CBS reduction to establish the required stereogenic centers. Other key steps involve Hor

Facile formation of tetrahydrofurans with multiple chiral centers using double iodoetherification of σ-symmetric diene acetals: short asymmetric total synthesis of rubrenolide and rubrynolide

A novel double intramolecular iodoetherification of σ-symmetric diene acetals from (R,R)-hydrobenzoin occurred in highly diastereoselective manners to give tetrahydrofuran moieties with multiple chiral centers in a one-pot operation. The chemoselective di

A double iodoetherification of σ-symmetric diene acetals for installing four stereogenic centers in a single operation: Short asymmetric total synthesis of rubrenolide

Tetrahydrofuran units with multiple chiral centers are formed in a highly diastereoselective manner through the one-pot double intramolecular haloetherification of σ-symmetric diene acetals (see scheme). The utility of the method was demonstrated by the s

Rubrenolide, total synthesis and revision of its reported stereochemical structure

In this paper the synthesis of the natural product rubrenolide is presented. Due to an error in the original proposed stereochemical structure of rubrenolide, the synthesis was not straightforward. Application of the photo-induced rearrangement of an appropriate epoxy diazomethyl ketone gave access to the precursor lactone with an ee of 91%. Coupling of this lactone with (4S)-2,2-dimethyl-[1,3]-dioxolane-4-carbaldehyde gave, after some additional steps, the final product that was identical with an authentic sample of the natural product.