171190-05-9

Upstream product

• 191935-28-1 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5S)-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-3,6-dihydroxyhexane-1,2,3-tricarboxylate 
• 208338-39-0 (1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(2,2-dimethylpropionyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane 
• 208338-43-6 (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane 
• 306281-54-9 (1S,3S,4S,5R,6R,7R)-1-((4R,5R)-4-Acetoxy-5-methyl-6-phenyl-hexyl)-6,7-bis-benzoyloxy-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 
• 208338-37-8 (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane 

Downstream Products

• 146389-62-0 (+)-zaragozic acid 

Relevant academic research and scientific papers

Total synthesis of zaragozic acid C: Implementation of photochemical C(sp3)-H acylation

Zaragozic acid C (1) was isolated as a potent squalene synthase inhibitor. The 2,8-dioxabicyclo[3.2.1]octane core of 1 is decorated with the three hydroxycarbonyl (C3,4,5), two hydroxy (C4,7), one acyloxy (C6), and one alkyl (C1) groups. Instal

Total synthesis of zaragozic acid C by an aldol-based strategy

A total synthesis of zaragozic acid C by a convergent strategy is described in which the key features include (1) the simultaneous creation of the C4 and C5 quaternary stereogenic centers by a Sn(OTf)2-promoted aldol coupling reaction between a

Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition Strategy

Ketal isomers avoided. The unique 2,8-dioxabicyclo[3.2.1 ]octane core of zaragozic acid C (1) was constructed in a Rh-catalyzed 1,3-dipolar cycloaddition of an alkyne to an ester carbonyl ylide. Another feature of this improved synthesis is the constructi

Total synthesis of (+)-zaragozic acid C

A total synthesis of (+)-zaragozic acid C is described. Key steps are an acid-mediated acetonide deprotection-dithiane removal-ketalisation procedure, providing selectively the 2,8-dioxabicyclo[3.2.1]octane core of the natural product, and the simultaneou

Total synthesis of the squalene synthase inhibitor zaragozic acid C

The total synthesis of zaragozic acid C has been achieved by a convergent strategy, wherein the key feature of the construction of 2,8-dioxabicyclo[3.2.1]octane core structure is a simultaneous creation of the C4 and C5 quaternary carbon centers by Sn(OTf

(+)-Zaragozic acid C: Synthesis and related studies

The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)2·H2O]2 for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of γ-alkoxy-α,β-trans enones, and (3) nucleophilic addition of Me3SiC≡CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.