macrosphelide A

Base Information

• Chemical Name: macrosphelide A
• CAS No.: 172923-77-2
• Molecular Formula: C16H22 O8
• Molecular Weight: 342.346

Synonyms:(+)-MacrosphelideA; Macrosphelide A

Chemical Property of macrosphelide A

Chemical Property:

• PSA: 119.36000
• LogP: 0.01940

Purity/Quality:

98%Min ^*data from raw suppliers

MacrosphelideA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of macrosphelide A

There total 112 articles about macrosphelide A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(7E,13E)-(4S,9R,10S,15R,16S)-15-Hydroxy-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (566203-50-7) → (+)-macrosphelide A (172923-77-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol0350689

Reference yield: 90.0%

(7E,13E)-(4S,9R,10S,15R,16S)-9,15-Bis-(2-methoxy-ethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione → (+)-macrosphelide A (172923-77-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja971657w

Reference yield: 90.0%

(5R,6S,11R,12S,16S)-(3E,9E)-5,11-bis[(2-methoxyethoxy)methyl]-6,12,16-trimethyl-1,7,13-trioxacyclohexadeca-3,9-diene-2,8,14-trione (196926-58-6) → (+)-macrosphelide A (172923-77-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 7.5h;

DOI:10.1016/j.tet.2005.02.022

upstream raw materials:

(7E,13E)-(4S,9R,10S,15R,16S)-15-Hydroxy-9-methoxymethoxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

(-)-dibenzyl macrosphelide A

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

(7E,13E)-(4S,9R,10S,15R,16S)-9,15-Bis-(4-methoxy-benzyloxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Downstream raw materials:

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

Refernces

Enantioselective total synthesis of macrosphelides A and e

10.1016/j.tet.2011.04.099

The study describes a concise and efficient enantioselective synthesis of the 16-membered trilactone macrolides, macrosphelides A and E, from (S)-lactic acid. The synthesis features the use of a previously unexplored ?-ketophosphonate derived from lactic acid and the Yamaguchi lactonization method. The study begins with the addition of a lithium anion to ethyl (S)-trityloxy lactate to form the ?-ketophosphonate, which is then reacted with allylglyoxalate to produce a,?-unsaturated esters. Reduction of these esters yields diastereomeric alcohols, which are subsequently transformed into the required acid and alcohol fragments through protection, saponification, and coupling reactions. The final macro trilactone is obtained via esterification, deprotection, and lactonization steps, yielding macrosphelides A and E with high purity. The overall yield of the synthesis is approximately 19%, and the spectral data of the synthesized compounds match those of the natural products. The procedure is operationally simple and high-yielding, making it suitable for the synthesis of various analogues for potential anti-cancer drug development.

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