Enantioselective synthesis and stereochemical revision of communiols A-C, antibacterial 2,4-disubstituted tetrahydrofurans from the coprophilous fungus Podospora communis.
The enantioselective synthesis of the originally proposed structure of communiol C, an antibacterial 2,4-disubstituted tetrahydrofuran natural product from the coprophilous fungus Podospora communis, and its epimer via the Sharpless asymmetric dihydroxylation as the source of chirality led us to propose that the genuine stereochemistry of communiol C should be 3R, 5R, and 6S. The synthesis of the (3R,5R,6S)-isomer of communiol C and its good accordance with natural communiol C in every respect enabled us to confirm the newly proposed (3R,5R,6S)-stereochemistry for communiol C. The stereochemistries of structurally-related natural products (communiols A and B) of the same microbial origin were also revised through their total synthesis.
Enomoto
Masaru
M
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Sendai, Japan.
Kuwahara
Shigefumi
S
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001688:Biological Products; D002087:Butyrates / Q000138:chemical synthesis* / Q000737:chemistry; D003437:Crotonates / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D048468:Podospora / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000900:Anti-Bacterial Agents; D001688:Biological Products; D002087:Butyrates; D003437:Crotonates; D005663:Furans; C531312:communiol A; C531313:communiol B; C531314:communiol C