460348-03-2

Upstream product

• 2237-36-7 4-methoxysalicylic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 109-89-7 diethylamine 
• 223511-04-4 tert-butyldimethylsilyl 2-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoate 

Downstream Products

• 460348-05-4 2-bromo-6-(tert-butyl-dimethyl-silanyloxy)-N,N-diethyl-4-methoxy-benzamide 
• 1276043-19-6 C₂₆H₃₇NO₈ 
• 460348-32-7 2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester 
• 460348-38-3 2-Hydroxy-6-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-hydroxy-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-4-methoxy-benzoic acid methyl ester 
• 460348-31-6 2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester 
• 460348-10-1 2-bromo-6-hydroxy-4-methoxy-benzoic acid 
• 460348-08-7 methyl 2-bromo-6-hydroxy-4-methoxybenzoate 

Relevant academic research and scientific papers

An enantioselective total synthesis of (+)-aigialospirol

(Chemical Equation Presented) A concise and enantioselective total synthesis of (+)-aigialospirol is described here, featuring the first complex natural product synthesis that employs a cyclic ketal-tethered ring-closing metathesis strategy and an unexpected stereoselective epimerization of a benzylic hydroxyl group. The 15-step synthetic sequence illustrates the proof-of-concept that such an approach can be competitive with the classical spiroketal formation in the natural product synthesis.

Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate

A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.

Two remarkable epimerizations imperative for the success of an asymmetric total synthesis of (+)-aigialospirol

Two remarkable epimerization processes were uncovered during our pursuit of an enantioselective synthesis of (+)-aigialospirol featuring a cyclic acetal tethered ring-closing metathesis. Through modeling, we were able to turn these two unexpected epimeriz

Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1

The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-Z1640-2) and hypothemycin gives a flexible access to related macrolides.