Enantioselective total synthesis and stereochemical revision of communiols E and F.
The enantioselective total synthesis of candidate structures for communiols E and F, novel bicyclic polyketides of fungal origin, was accomplished using a Lewis acid-mediated ring closure reaction of an allylsilane intermediate as the key step. Comparison of the spectral data of the synthetic materials with those of natural communiols E and F, coupled with biosynthetic considerations, led to the conclusion that the stereochemistry of communiols E and F should be (2S,5S,7R, 8S,11R)- and (5S,7R,8S,11R)-forms, respectively.
Enomoto
Masaru
M
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
Kuwahara
Shigefumi
S
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D013053:Spectrophotometry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009930:Organic Chemicals; C520452:communiol E; C520453:communiol F