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Volumn 74, Issue 11, 2009, Pages 4024-4040

Synthetic studies on gambieric acids, potent antifungal polycyclic ether natural products: Reassignment of the absolute configuration of the nonacyclic polyether core by NMR analysis of model compounds

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ANTI-FUNGAL; CHEMICAL EQUATIONS; CONVERGENT SYNTHESIS; DIASTEREOSELECTIVE; MODEL COMPOUND; NATURAL PRODUCTS; NMR ANALYSIS; NMR CHEMICAL SHIFTS; NMR DATA; POLYCYCLIC ETHERS; RING FRAGMENTS; RING MODEL; SUZUKI-MIYAURA COUPLING; SYNTHETIC STUDY; TETRA-HYDROFURAN; VINYL IODIDES;

EID: 66249130049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900332q     Document Type: Article
Times cited : (24)

References (51)
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    • The numbering of carbon atoms of all compounds in this paper corresponds to that of the natural product
    • The numbering of carbon atoms of all compounds in this paper corresponds to that of the natural product.
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    • It is interesting that the difference of the C12 position between hydroxy alkenes 2 and 19 affected the apparent diastereoselectivity of their respective bromoetherifications. However, we notice that the net yield of tricyclic compound 15 was 70% from hydroxy alkene 2, which is comparable to that of tricyclic compound 37 (69% yield from hydroxy alkene 19). Although the reason for this result is not clear, we speculate that the undesired mode of cyclization (i.e., Figure 2, TS-B) of 19 would result in decomposition of the substrate. Similarly, bromoetherification/reduction of hydroxy alkene 48 proceeded with a seemingly better diastereoselectivity (dr = 3.5:1) than that of hydroxy alkene 63 (dr = 2:1), but the net yield of the desired tricyclic compound 49 (47%) was almost the same as that of 65 (49%) (vide infra)
    • It is interesting that the difference of the C12 position between hydroxy alkenes 2 and 19 affected the apparent diastereoselectivity of their respective bromoetherifications. However, we notice that the net yield of tricyclic compound 15 was 70% from hydroxy alkene 2, which is comparable to that of tricyclic compound 37 (69% yield from hydroxy alkene 19). Although the reason for this result is not clear, we speculate that the undesired mode of cyclization (i.e., Figure 2, TS-B) of 19 would result in decomposition of the substrate. Similarly, bromoetherification/reduction of hydroxy alkene 48 proceeded with a seemingly better diastereoselectivity (dr = 3.5:1) than that of hydroxy alkene 63 (dr = 2:1), but the net yield of the desired tricyclic compound 49 (47%) was almost the same as that of 65 (49%) (vide infra).
  • 47
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    • 5N. See the Supporting Information for details
    • 5N. See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.