701261-90-7

Upstream product

• 828-01-3 D-phenyllactic acid 
• 146235-25-8 (2R)-2-acetoxy-3-phenylpropanoic acid 
• 13057-17-5 bromethyl methyl ether 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 673-06-3 D-(R)-phenylalanine 

Downstream Products

• 701261-77-0 (tert-butoxycarbonylimino-{3-[2-({6-methoxymethoxy-1-[2-(2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carbonyl}-amino)-ethyl]-2,5-dihydro-pyrrol-1-yl}-methyl)-carbamic acid tert-butyl ester 
• 701261-96-3 2-tert-butoxycarbonylamino-5-[3-({6-methoxymethoxy-1-[2-(2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carbonyl}-amino)-propylidene]-5,6-dihydro-4H-pyrimidine-1-carboxylic acid tert-butyl ester 
• 701261-92-9 (2S,3aS,6R,7aS)-6-Acetoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-94-1 (2S,3aS,6R,7aS)-6-Methoxymethoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid 
• 701261-75-8 (2S,3aS,6R,7aS)-6-Methoxymethoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-93-0 (2S,3aS,6R,7aS)-6-Hydroxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-91-8 (R)-2-((R)-2-Methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionic acid benzyl ester 
• 701261-74-7 (R)-2-((R)-2-Methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionic acid 
• 282551-84-2 MOM-D-phenyllactic acid 

Relevant academic research and scientific papers

Total Synthesis of (+)-Prunustatin A: Utility of Organotrifluoroborate-Mediated Prenylation and Shiina MNBA Esterification and Macrolactonization to Avoid a Competing Thorpe-Ingold Effect Accelerated Transesterification

A convergent total synthesis of (+)-prunustatin A is described through the assembly of two key fragments and a macrolactonization. Shiina MNBA couplings were used for the formation of each of the four ester bonds in the tetralactone ring, including the key macrocyclization which was essential to minimize competing Thorpe-Ingold accelerated transesterification. Other key steps included an organoboron-based prenylation using potassium prenyltrifluoroborate and a carbonyldiimidazole-mediated coupling to form the salicylamide.

The N-Acyloxyiminium Ion Aza-Prins Route to Octahydroindoles: Total Synthesis and Structural Confirmation of the Antithrombotic Marine Natural Product Oscillarin

The first enantiocontrolled total synthesis of the marine natural product oscillarin is described. The proposed structure and absolute configuration of oscillarin is thus confirmed, and a previously assigned structure of a subunit was shown to be incorrect. The X-ray structure of an oscillarin-thrombin complex was resolved at 2.0 A resolution, which validated its potent inhibitory activity against the enzyme with an IC50 = 28 nM. Methodology was developed for the synthesis of enantiopure octahydroindole-2-carboxylic acids with usable functionality at C-6. The method consists of the halocarbocyclization of N-acyloxyiminium ions containing an olefinic tether in the presence of fin tetrachloride or fin tetrabromide. This N-acyloxyiminium ion aza-Prins carbocyclization proved to be general for the construction of octahydroindole and perhydroquinoline 2-carboxylic acids. Mechanistic rationales are based on an antiperiplanar attack of the terminal alkene on the iminium ion, leading to an incipient secondary carbocation which is trapped by halide via an equatorial attack. X-ray crystal structures of products corroborate the expected stereochemistry.