Synthesis of a monocyclic core of the antifungal sordarins

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8553-8556

  Cuevas, Juan C ^a   Martos, José L ^a  

^a GLAXOSMITHKLINE   (Spain)

Author keywords

Antifungals; Cyclopentanes; Enantiospecificity

Indexed keywords

ANTIFUNGAL AGENT; SORDARICIN; SORDARIN; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; CELL TRANSFORMATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; NONHUMAN; OXIDATION; PROTEIN SYNTHESIS INHIBITION; REVIEW;

EID: 0032511932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01910-8     Document Type: Article

References (12)

1. [1] Domínguez JM, Capa L, Serramía MJ, Mendoza A, Viana JM, Garcia-Bustos JF, Martín JJ. Abstracts of Papers. 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, 1997; F-55.
2. [2] Herreros E, Martínez CM, Almela MJ, Lozano S, Gómez de las Heras F, Gargallo D. Abstracts of Papers, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, 1997; F-57.
3. 2H is certainly uncommon since this functional grouping is normally found as cyclic hydroxylactone. Its presence in these molecules is likely due to a high dihedral angle (67° for sordaricin and 95° for its cyclopentanic analogue). These structures were modelled and conformationally optimized by semi-empirical methods.
4. [4] Commercially available (Aldrich Chem. Co.)
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8. 3/DMSO) reported by Bauer and Macomber (Bauer DP, Macomber RS. J. Org. Chem. 1975; 13: 1990-1992).
9. 3/DMSO) reported by Bauer and Macomber (Bauer DP, Macomber RS. J. Org. Chem. 1975; 13: 1990-1992).
10. 3 gave rise to a mixture of reduced compounds. Hemiacetal 13 could only be isolated in 28% yield. (equation presented)
11. [10] For the use of natural camphors in the synthesis of chiral natural products, see: Money T. Nat. Prod. Rep. 1985;2: 253-289.
12. [11] All new compounds gave satisfactory spectroscopic and analytical data.