The Synthesis of (+)-Pisiferol and (+)-Pisiferal
Publication type: Journal Article
Publication date: 1983-07-01
scimago Q2
wos Q2
SJR: 0.678
CiteScore: 7.0
Impact factor: 3.8
ISSN: 00092673, 13480634
General Chemistry
Abstract
Reduction of abieta-8,11,13,-trien-6-one with lithium aluminium hydride, followed by treatment with lead tetraacetate and iodine, affored 6β,20-epoxyabieta-8,11,13-triene. This was converted into a separable mixture of abieta-8,11,13-trien-20-ol (13) and 5βH-abieta-8,11,13-trien-20-ol (14) by a series of reactions; ether cleavage with acetic p-toluenesulfonic anhydride, catalytic hydrogenation, and reduction with lithium aluminium hydride. Acetylation of 13 and 14 gave the corresponding acetates, 20-acetoxyabieta-8,11,13-triene (11) and 20-acetoxy-5βH-abieta-8,11,13-triene (12). Friedel-Crafts acylation of 11 with acetyl chloride in the presence of anhydrous aluminium chloride afforded 20-acetoxy-12-acetylabieta-8,11,13-triene, which was converted into pisiferol by oxidation with m-chloroperbenzoic acid and subsequent treatment with lithium aluminium hydride. The synthetic pisiferol was oxidized with Jones reagent to give pisiferal. Similarly, 5βH-abieta-8,11,13-triene-12,20-diol was synthesized from 12. ...
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
|
|
|
Tetrahedron Letters
5 publications, 22.73%
|
|
|
Phytochemistry
4 publications, 18.18%
|
|
|
Tetrahedron
2 publications, 9.09%
|
|
|
Journal of the Chemical Society Perkin Transactions 1
2 publications, 9.09%
|
|
|
Fitoterapia
1 publication, 4.55%
|
|
|
Chemischer Informationsdienst
1 publication, 4.55%
|
|
|
Helvetica Chimica Acta
1 publication, 4.55%
|
|
|
Journal of Heterocyclic Chemistry
1 publication, 4.55%
|
|
|
Bulletin of the Korean Chemical Society
1 publication, 4.55%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 4.55%
|
|
|
Synthetic Communications
1 publication, 4.55%
|
|
|
Total Synthesis of Natural Products
1 publication, 4.55%
|
|
|
1
2
3
4
5
|
Publishers
|
2
4
6
8
10
12
|
|
|
Elsevier
12 publications, 54.55%
|
|
|
Wiley
5 publications, 22.73%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 13.64%
|
|
|
Taylor & Francis
1 publication, 4.55%
|
|
|
2
4
6
8
10
12
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
22
Total citations:
22
Citations from 2024:
0
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
MATSUMOTO T., Endo Y., Okimoto M. The Synthesis of (+)-Pisiferol and (+)-Pisiferal // Bulletin of the Chemical Society of Japan. 1983. Vol. 56. No. 7. pp. 2018-2022.
GOST all authors (up to 50)
Copy
MATSUMOTO T., Endo Y., Okimoto M. The Synthesis of (+)-Pisiferol and (+)-Pisiferal // Bulletin of the Chemical Society of Japan. 1983. Vol. 56. No. 7. pp. 2018-2022.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1246/bcsj.56.2018
UR - https://doi.org/10.1246/bcsj.56.2018
TI - The Synthesis of (+)-Pisiferol and (+)-Pisiferal
T2 - Bulletin of the Chemical Society of Japan
AU - MATSUMOTO, TAKASHI
AU - Endo, Yoshinori
AU - Okimoto, Masaru
PY - 1983
DA - 1983/07/01
PB - Oxford University Press
SP - 2018-2022
IS - 7
VL - 56
SN - 0009-2673
SN - 1348-0634
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1983_MATSUMOTO,
author = {TAKASHI MATSUMOTO and Yoshinori Endo and Masaru Okimoto},
title = {The Synthesis of (+)-Pisiferol and (+)-Pisiferal},
journal = {Bulletin of the Chemical Society of Japan},
year = {1983},
volume = {56},
publisher = {Oxford University Press},
month = {jul},
url = {https://doi.org/10.1246/bcsj.56.2018},
number = {7},
pages = {2018--2022},
doi = {10.1246/bcsj.56.2018}
}
Cite this
MLA
Copy
MATSUMOTO, TAKASHI, et al. “The Synthesis of (+)-Pisiferol and (+)-Pisiferal.” Bulletin of the Chemical Society of Japan, vol. 56, no. 7, Jul. 1983, pp. 2018-2022. https://doi.org/10.1246/bcsj.56.2018.