TY - JOUR
T1 - Enantioselective synthesis and stereochemical revision of communiols A-C, antibacterial 2,4-disubstituted tetrahydrofurans from the coprophilous fungus Podospora communis
AU - Enomoto, Masaru
AU - Kuwahara, Shigefumi
N1 - Funding Information:
We are grateful to Prof. Gloer (University of Iowa) for providing the copies of the NMR spectra of communiols A–C. We also thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (no. 19380065).
PY - 2008
Y1 - 2008
N2 - 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.
AB - 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.
KW - Antibacterial
KW - Asymmetric dihydroxylation
KW - Communiol
KW - Enantioselective synthesis
KW - Stereochemical revision
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U2 - 10.1271/bbb.80173
DO - 10.1271/bbb.80173
M3 - Article
C2 - 18603786
AN - SCOPUS:48049100148
SN - 0916-8451
VL - 72
SP - 1921
EP - 1928
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 7
ER -