TY - JOUR
T1 - Total syntheses of (+)-1893B and its three diastereomers and evaluation of their biological activities
AU - Yasui, Hiroyuki
AU - Hirai, Kunihiro
AU - Yamamoto, Shun
AU - Takao, Ken Ichi
AU - Tadano, Kin Ichi
N1 - Funding Information:
Acknowledgement This work was supported by Grant-in-Aid for the 21st Century COE program “KEIO Life Conjugate Chemistry” from MEXT, Japan. We thank Infectious Disease Research Labs., Meiji Seika Kaisha, Ltd., for performing the biological assays. We thank Professors Yongcheng Lin (Zhongshan University) and Guangying Chen (City University of Hong Kong) for providing spectral data of the natural product.
PY - 2006/8
Y1 - 2006/8
N2 - The total syntheses of natural (+)-1893B (2) and three other diastereomers 14, 18, and 21 were accomplished. Starting from the sequential metathesis product 5 prepared in turn from a 7-oxanorbornene derivative (+)-4, 2 was synthesized by means of an epoxy-ring opening of 9a with trimethylsilylacetylide followed by Wacker-type oxidation of the resulting alkyne 10 for the construction of the γ-lactone moiety. By applying the same synthetic sequence, three additional diastereomers of 2, 14, 18, and 21 were also synthesized. The biological activities of previously synthesized 1893A (1), 1893B (2), and the diastereomers of 1893B 14, 18, and 21 were investigated.
AB - The total syntheses of natural (+)-1893B (2) and three other diastereomers 14, 18, and 21 were accomplished. Starting from the sequential metathesis product 5 prepared in turn from a 7-oxanorbornene derivative (+)-4, 2 was synthesized by means of an epoxy-ring opening of 9a with trimethylsilylacetylide followed by Wacker-type oxidation of the resulting alkyne 10 for the construction of the γ-lactone moiety. By applying the same synthetic sequence, three additional diastereomers of 2, 14, 18, and 21 were also synthesized. The biological activities of previously synthesized 1893A (1), 1893B (2), and the diastereomers of 1893B 14, 18, and 21 were investigated.
KW - Oxabicyclo[4.2.1]nona-2,4-diene
KW - Total synthesis
KW - γ-lactone
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U2 - 10.1038/ja.2006.64
DO - 10.1038/ja.2006.64
M3 - Article
C2 - 17080681
AN - SCOPUS:33749480188
SN - 0021-8820
VL - 59
SP - 456
EP - 463
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 8
ER -