Macquarimicin A
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| Category | Antibiotics |
| Catalog number | BBF-02286 |
| CAS | 165561-14-8 |
| Molecular Weight | 330.37 |
| Molecular Formula | C19H22O5 |
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Description
It is produced by the strain of Micromonospora chalcea. It's an antibiotic.
Specification
| Synonyms | 2,5-Ethanoindeno[4,5-e]oxecin-3,11,15-trione,5,6,7,8,8a,10a,12,13,13a,13b-decahydro-7-hydroxy-12-methyl-, (1Z,5R*,7R*,8aS*,10aS*,12R*,13aR*,13bS*)-(+)- |
| IUPAC Name | (1Z,3S,4R,6R,8S,11S,13R,15R)-13-hydroxy-6-methyl-16-oxatetracyclo[13.2.2.03,11.04,8]nonadeca-1,9-diene-7,17,18-trione |
| Canonical SMILES | CC1CC2C(C1=O)C=CC3C2C=C4C(=O)CC(CC(C3)O)OC4=O |
| InChI | InChI=1S/C19H22O5/c1-9-4-15-13(18(9)22)3-2-10-5-11(20)6-12-7-17(21)16(8-14(10)15)19(23)24-12/h2-3,8-15,20H,4-7H2,1H3/b16-8-/t9-,10-,11-,12-,13+,14+,15+/m1/s1 |
| InChI Key | BYUKEFZLYIFNCB-IXYWQHHVSA-N |
Reference Reading
1. Synthetic study of macquarimicins: highly stereoselective construction of the AB-ring system
R Munakata, T Ueki, H Katakai, K I Takao, K I Tadano Org Lett. 2001 Sep 20;3(19):3029-32. doi: 10.1021/ol016449u.
The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide. Reaction: see text.
2. Total synthesis of (+)-macquarimicin A
Ryosuke Munakata, Hironori Katakai, Tatsuo Ueki, Jun Kurosaka, Ken-ichi Takao, Kin-ichi Tadano J Am Chem Soc. 2003 Dec 3;125(48):14722-3. doi: 10.1021/ja038732p.
The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis features a transannular Diels-Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.
3. Total synthesis of macquarimicins using an intramolecular Diels-Alder approach inspired by a biosynthetic pathway
Ryosuke Munakata, Hironori Katakai, Tatsuo Ueki, Jun Kurosaka, Ken-Ichi Takao, Kin-Ichi Tadano J Am Chem Soc. 2004 Sep 15;126(36):11254-67. doi: 10.1021/ja048320w.
A total synthesis of the macquarimicins A-C (1-3), novel natural products with intriguing tetra- or pentacyclic frameworks, has been achieved. The synthesis features an extensive investigation of the biosynthesis-based intramolecular Diels-Alder (IMDA) reactions of (E,Z,E)-1,6,8-nonatrienes. Considering possible biosynthetic sequences, four types of substrates were synthesized, and their IMDA reactions were examined. From one of the four substrates, the total synthesis was achieved via a transannular Diels-Alder reaction, which led to the stereoselective construction of the unique molecular framework. The convergent and efficient synthetic pathway afforded (+)-1 in 27 linear steps with 4.3% and 9.9% overall yields from readily available ethyl (2E,4S)-4,5-(isopropylidene)dioxy-2-pentenoate (22) and (R)-epichlorohydrin (30), respectively. Furthermore, efficient syntheses of 2, 3, and the 9-epi-cochleamycins A (57) and B (58) were accomplished. Additionally, the present work established the absolute stereochemistry of macquarimicins and revised the C(2)--C(3) geometry of 1.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
