| Autor: |
Amit Mondal, Nirmal Saha, Syed Masood Husain |
| Jazyk: |
angličtina |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Tetrahedron Chem, Vol 3, Iss , Pp 100030- (2022) |
| Druh dokumentu: |
article |
| ISSN: |
2666-951X |
| DOI: |
10.1016/j.tchem.2022.100030 |
| Popis: |
Synthesis of complex dimeric natural products (−)-luteoskyrin and (−)-deoxyluteoskyrin isolated from P. islandicum Sopp nearly 70 years ago, remained a challenge until now. Their biosynthesis had been proposed to involve dimerization using a putative intermediate dihydrocatenarin as a key step. In the current work, we employed a chemoenzymatic strategy to synthesize (R)-dihydrocatenarin using an anthrol reductase of T. islandicus. Its homodimerization in the presence of molecular oxygen gave (−)-rubroskyrin, which on Michael reaction led to the first total synthesis of (−)-luteoskyrin in an overall yield of 21%. In contrast, the heterodimerization between (R)-dihydrocatenarin and (R)-dihydroemodin led to non-natural, (−)-deoxyrubroskyrin analogue, while the use of molecular oxygen gave natural (−)-deoxyrubroskyrin. Both (−)-deoxyrubroskyrin and its analogue on treatment with pyridine gave (−)-deoxyluteoskyrin with an overall yield of up to 10%. The presence of dihydrocatenarin in P. islandicum NRRL 1036 culture is verified through mass spectrometry, which implied a similar biosynthetic pathway. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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