896104-74-8

Upstream product

• 896104-51-1 (E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 1117-97-1 N,0-dimethylhydroxylamine 

Downstream Products

• 896104-52-2 (E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one 
• 896104-53-3 (4S,5S)-5-[3-(4-Methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-2-enone 
• 896104-76-0 (2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-cyclopentanone 
• 896104-54-4 Trifluoro-methanesulfonic acid (4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-1-enyl ester 
• 896104-64-6 (1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde 
• 896104-60-2 {(1S,2S,3R)-2-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-((4S,5S)-5-but-3-ynyl-4-methyl-cyclopent-1-enyl)-but-2-enyl]-3-isopropyl-1-methyl-cyclopentyl}-methanol 
• 896104-55-5 (Z)-4-[(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclopentyl]-2-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-1-enyl}-but-2-enoic acid methyl ester 
• 896104-77-1 (Z)-4-[(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclopentyl]-2-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-1-enyl}-but-2-en-1-ol 
• 896104-63-5 (2Z,11E)-(5S,6R,9S,10R,15S,16S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-ol 
• 896429-17-7 (2Z,11E)-(5S,6R,9S,10S,15S,16S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-ol 
• 896104-62-4 (1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-5-((E)-4-iodo-3-methyl-but-3-enyl)-4-methyl-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde 
• 896104-61-3 ((1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-5-((E)-4-iodo-3-methyl-but-3-enyl)-4-methyl-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentyl)-methanol 
• 896104-68-0 Carbonic acid (2Z,11E)-(5S,6R,9S,10R,15S,16S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-yl ester methyl ester 
• 896104-91-9 Carbonic acid (2Z,11E)-(5S,6R,9S,10S,15S,16S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-yl ester methyl ester 

Relevant academic research and scientific papers

A synthetic approach toward nitiol: Construction of two 1,22-dihydroxynitianes

Synthetic work toward the total synthesis of nitiol has culminated in the construction of two epimeric hydroxylated derivatives, the 1,22- dihydroxynitianes. Key stereodefining steps in the construction of the A-ring fragment (13) were the use of a siloxy-epoxide rearrangement reaction, a Pauson-Khand reaction, a Norrish 1 photochemical cleavage reaction, and a highly regio- and stereoselective hydrostannylation reaction of an ynoate. The stereochemistry of the synthetically challenging C-ring fragment (20) was established using an Ireland-Claisen reaction and a Grubbs ring-closing metathesis process as key steps. The 12-membered B-ring of the nitiane skeleton was constructed using a copper-promoted Stille cross-coupling and a Kishi-Hiyama-Nozaki carbonyl addition reaction. Unfortunately, the carbonyl addition reaction produced hydroxyl functionality that could not be selectively removed. Consequently, a synthesis of epimeric 1,22-dihydroxynitianes, which are compounds that are structural hybrids of two natural products, nitiol and variculanol, was completed.

A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides

The conversion of sterically hindered carboxylic acids to N-methoxy-N-methyl amides can be efficiently carried out with 1.1 equiv of methanesulfonyl chloride, 3 equiv of triethylamine, and 1.1 equiv of N-methoxy-N-methylamine. Yields for this process rang