TY - JOUR
T1 - Structures and Synthesis of Hitoyopodins
T2 - Bioactive Aromatic Sesquiterpenoids Produced by the Mushroom Coprinopsis cinerea
AU - Otaka, Junnosuke
AU - Shimizu, Takeshi
AU - Futamura, Yushi
AU - Hashizume, Daisuke
AU - Osada, Hiroyuki
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/10/5
Y1 - 2018/10/5
N2 - The structures of sesquiterpenoids hitoyopodin A (1) and its hydroxy derivatives 2 and 3 from the mushroom Coprinopsis cinerea are reported. Their absolute structures (1-3) with a benzoxabicyclo[3.2.1]octane core were determined by spectroscopy, X-ray crystallography, and total synthesis of 1. Compound 1 displays antiproliferative activity against HL-60 cancer cells and the malarial parasite Plasmodium falciparum. It is proposed that 1 acts as a crucial precursor in the biosynthesis of 2, 3, and lagopodins.
AB - The structures of sesquiterpenoids hitoyopodin A (1) and its hydroxy derivatives 2 and 3 from the mushroom Coprinopsis cinerea are reported. Their absolute structures (1-3) with a benzoxabicyclo[3.2.1]octane core were determined by spectroscopy, X-ray crystallography, and total synthesis of 1. Compound 1 displays antiproliferative activity against HL-60 cancer cells and the malarial parasite Plasmodium falciparum. It is proposed that 1 acts as a crucial precursor in the biosynthesis of 2, 3, and lagopodins.
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U2 - 10.1021/acs.orglett.8b02788
DO - 10.1021/acs.orglett.8b02788
M3 - Article
C2 - 30234313
AN - SCOPUS:85053824122
SN - 1523-7060
VL - 20
SP - 6294
EP - 6297
JO - Organic Letters
JF - Organic Letters
IS - 19
ER -