Synthesis of Xyloketal A, B, C, D, and G Analogues

• Published in: Journal of organic chemistry Vol. 71; no. 4; pp. 1620 - 1625
• Main Authors: Pettigrew, Jeremy D, Wilson, Peter D
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.02.2006; Amer Chemical Soc
• Subjects: Biological Products - chemical synthesis; Catalysis; Chemistry; Chemistry, Organic; Exact sciences and technology; Furans - chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Phenols - chemistry; Physical Sciences; Preparations and properties; Pyrans - chemical synthesis; Science & Technology; ACID; CHINA SEA COAST; FUNGUS XYLARIA SP; METABOLITE; Electrophilic substitution; Furan derivatives; Phenols; Natural product; Ethyl ether; Oxygen heterocycle; Aromatic substitution; Chemical synthesis; Chemical substitution
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo052371+

A series of demethyl analogues of the natural products xyloketal A, B, C, D, and G have been prepared in a notably direct manner from 3-hydroxymethyl-2-methyl-4,5-dihydrofuran and a series of corresponding phenols. These syntheses featured a boron trifluoride diethyl etherate-promoted electrophilic aromatic substitution reaction as a key step. In the case of the synthesis of analogues of xyloketal A, the process was found to be highly efficient (up to 93% yield). The optimized isolated yield of these reaction products is remarkable in view of the fact that this transformation involves, minimally, six individual reactions. Moreover, these synthetic studies provide significant insight into the possible biogenic origin of the xyloketal natural products.