Synthesis of the Proposed Structure of Fudecalone, an Anticoccidial Drimane Terpenoid-Reference-Cited by-同舟云学术

Synthesis of the Proposed Structure of Fudecalone, an Anticoccidial Drimane Terpenoid

Published:1999-09-14 Issue:7 Volume:1 Page:1079-1080
ISSN:1523-7060
Container-title:Organic Letters
language:en
Short-container-title:Org. Lett.

Author:

Watanabe Hidenori¹,Furuuchi Takeshi¹,Yamaguchi Takahiro¹,Kitahara Takeshi¹

Affiliation:

1. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/ol990882a

Reference9 articles.

1. In CDCl3, the hemiacetal of the synthetic1equilibrated to an α/β = 1:3 mixture: 1H NMR (500 MHz, in CDCl3) major isomer, δ 5.90 (br m, 1H, H-5), 4.94 (s, 1H, H-1), 4.33 (t,J= 9.0 Hz, 1H, H-3), 4.09 (dd,J= 9.0, 3.0 Hz, 1H, H-3), 2.72 (br d,J= 9.0 Hz, 1H, H-3a), 2.22 (s, 1H, H-6a), 1.91 (t,J= 1.0 Hz, 3H, H-11), 1.71 (m, 1H, H-10), 1.50−1.70 (m, 2H, H2-9), 1.46 (m, 1H, H-8), 1.30 (m, 1H, H-8), 1.24 (m, 1H, H-10), 1.05 (s, 3H, H-13), 0.76 (s, 3H, H-12); minor isomer, δ 5.90 (br m,J= 1.0 Hz, 1H, H-5), 4.98 (s, 1H, H-1), 4.33 (dd,J= 9.0, 7.0 Hz, 1H, H-3), 3.97 (br d,J= 9.0 Hz, 1H, H-3), 2.81 (br d,J= 7.0 Hz, 1H, H-3a), 2.14 (s, 1H, H-6a), 1.95 (t,J= 1.0 Hz, 3H, H-11), 1.01 (s, 3H, H-13), 0.79 (s, 3H, H-12);13C NMR (125 MHz, in CDCl3) major isomer, δ 200.80, 156.53, 128.47, 107.38, 70.00, 54.46, 48.44, 44.10, 41.54, 34.73, 33.40, 31.32, 24.60, 22.29, 18.16; minor isomer, δ 201.00, 158.84, 128.47, 102.71, 68.51, 55.46, 46.68, 46.20, 41.26, 33.79, 31.48, 25.88, 24.09, 22.01, 18.37.

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