43043-17-0

Upstream product

• 62856-68-2 (3S,4S,7S,8S)-3,7-dimethyl-4,8-bis((2R,4R)-4-methylhexan-2-yl)-1,5-dioxocane-2,6-dione 
• 273738-41-3 (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate 
• 176900-63-3 (2S,4R)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentyl acetate 
• 90270-02-3 (2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate 
• 2121-69-9 (2R,4S)-2,4-dimethylpentane-1,5-diol 
• 1373758-77-0 ethyl (4R,6R,E)-4,6-dimethyloct-2-enoate 
• 1373758-76-9 tert-butyl[(2R,4R)-2,4-dimethylhexyloxy]diphenylsilane 
• 1174752-29-4 (2R,3S,4R,6R)-2,4,6-trimethyl-octane-1,3-diol 
• 1174752-33-0 [(2S,3S)-3-((1R,3R)-1,3-dimethyl-pentyl)-oxiranyl]-methanol 
• 1174752-32-9 (E)-(4R,6R)-4,6-dimethyl-oct-2-en-1-ol 
• 1174752-40-9 (2S,3S,4R,6R)-3-benzyloxy-2,4,6-trimethyl-octanoic acid (1S,2R,4R)-1-((S)-1-carboxyethyl)-2,4-dimethyl-hexyl ester 
• 87106-25-0 (R)-(+)-1-iodo-2-methylbutane 
• 159254-33-8 (2R)-(E)-2,4-dimethyl-4-hexen-1-ol 
• 159254-32-7 (2'S,4S)-(E)-3-(2',4'-dimethyl-4'-hexenoyl)-4-isopropyl-1,3-oxazolidin-2-one 

Downstream Products

• 103675-21-4 (2S,3S,4R,6R)-3-Hydroxy-2,4,6-trimethyl-octanoic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester 

Relevant academic research and scientific papers

Synthesis of the Lichen Metabolite (+)-Bourgeanic Acid and Conformational Analysis of Its Dilactone

An enantiospecific synthesis of the depside (+)-bourgeanic acid via (-)-hemibourgeanic acid defines the letter as (2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid and the former as its self-esterification product.Conformational analysis of the dilactone derived from bourgeanic acid shows that the eight-membered ring adopts a crown conformation with C2 symmetry and all substituents in equatorial orientation.

Chemoenzymatic approach to the total synthesis of (+)-bourgeanic acid

A highly stereoselective total synthesis of (+)-bourgeanic acid has been accomplished by an enzymatic desymmetrization approach to create two methyl chiral centers. Other key steps involved in this approach are a Wittig reaction, a Gilman reaction, and TE

Total synthesis of (+)-bourgeanic acid utilizing desymmetrization strategy

A highly stereoselective total synthesis of an aliphatic depside (+)-bourgeanic acid via (-)-hemibourgeanic acid and bourgeanic lactone is described. The key steps involved in this synthesis are desymmetrization of bicyclic olefin with Brown's asymmetric

Total synthesis of (+)-bourgeanic acid utilizing o-DPPB-directed allylic substitution

The lichen metabolite (+)-bourgeanic acid has been synthesized utilizing a new strategy for the construction of propionate motifs relying on the o-DPPB-directed copper-mediated allylic substitution. This synthesis features the o-DPPB-directed allylic substitution employing a chiral Grignard reagent, Sharpless asymmetric epoxidation, and reductive epoxide ring opening with a higher order dimethylcuprate to set the four stereogenic centers of the aliphatic depside.

Synthesis of the Aliphatic Depside (+)-Bourgeanic Acid

The lichen metabolite (+)-bourgeanic acid (1) was synthesized in 12 steps and 3.4percent overall yield from (R)-2-methyl-1-iodobutane (53) by a sequence which confirmed that this aliphatic depside is the self-esterification product of (2S,3S,4R,6R)-2,4,6-trimethyl-3-hydroxyoctanoic acid.Alkylation of the enolate of (S)-N-propionylprolinol (48) with 53 gave the amide 60 which was transformed to (2R,4R)-2,4-dimethylhexanal (4).The latter was reacted with the crotylboronate 68, prepared from (S,S)-(-)-diisopropyl tartrate, to afford (3R,4S,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol (65) as the major diastereomer.Protection followed by ozonolysis and oxidation furnished (-)-hemibourgeanic acid (2).The β-lactone 73 derived from 2 was used to acylate 65, and the resulting ester 74 was subjected to oxidative ozonolysis to yield (+)-1.