172923-77-2

Basic information

• Product Name: macrosphelide A
• Synonyms: macrosphelide A
• CAS NO: 172923-77-2
• Molecular Formula: C₁₆H₂₂O₈
• Mol File: 172923-77-2.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: macrosphelide A(CAS DataBase Reference)
• NIST Chemistry Reference: macrosphelide A(172923-77-2)
• EPA Substance Registry System: macrosphelide A(172923-77-2)

Safety Data

• Hazardous Substances Data: 172923-77-2(Hazardous Substances Data)

Usage

Uses

Macrosphelide A is a cytotoxic agent of the family of Macrosphelides A-G which is used in antibacterials as they inhibit the growth of ascomycetes, basidomycetes and other gram-positive bacteria. Inhibits cell-cell adhesion.

Upstream product

• 642075-92-1 (E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (E)-(1S,2R)-2-(2-methoxy-ethoxymethoxy)-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 642075-90-9 (E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 642075-91-0 (E)-(4R,5S)-5-Hydroxy-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 642075-89-6 tert-Butyl-[(1S,2R)-2-(2-methoxy-ethoxymethoxy)-1-methyl-but-3-ynyloxy]-dimethyl-silane 
• 350848-03-2 methyl (S)-3-(4-methoxybenzyloxy)butanoate 
• 640283-59-6 4-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-pent-1-yn-3-one 
• 566203-47-2 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-(tert-butyldimethylsilyloxy)-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 
• 566203-39-2 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 
• 566203-48-3 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-hydroxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 
• 566203-49-4 (-)-1-(3-hydroxy-1-penten-4-yloxycarbonyl)prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 
• 566203-46-1 (3R,4S)-3-(4-methoxybenzyloxy)-1-penten-4-yl (3S)-3-(tert-butyldimethylsilyloxy)butanoate 
• 566203-43-8 5-(tert-butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid ethyl ester 
• 566203-40-5 (3R,4S)-3-(4-methoxybenzyloxy)-1-penten-4-yl (3S)-3-hydroxybutanoate 
• 305817-98-5 (3R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-(trimethylsilyl)-pent-1-yn-3-ol 

Downstream Products

• 172923-78-3 (5R,6S,12S,16S)-(3E,9E)-5-hydroxy-6,12,16-trimethyl-1,7,13-trioxacyclohexadeca-3,9-diene-2,8,11,14-tetraone 

Relevant articles and documents

Total synthesis of macrosphelide A by way of palladium-catalyzed carbonylative esterification

We achieved the total synthesis of macrosphelide A, as part of a combinatorial library of its analogues. The key intermediate, the seco-acid derivative, was prepared from the corresponding vinyl iodide using sequential carbonylative esterification.

General Stereodivergent Enantioselective Total Synthetic Approach toward Macrosphelides A-G and M

A straightforward enantioselective total synthesis algorithm for the preparation of 8 out of 13 macrosphelides within 9-11 steps starting from tert-butyl sorbate is presented. The use of a cyclic sulfate as both protecting and reactivity directing group is the key element within this algorithm. A high-pressure transesterification allows for the selective ring-enlargement of the 15-membered macrosphelides into the 16-membered counterparts. The absolute configurations of the natural products were unambiguously assigned both by the chemical synthesis and by X-ray structure analysis.

Total Synthesis of Macrosphelides A, B, and E: First Application of Ring-Closing Metathesis for Macrosphelide Synthesis

A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.