2024-03-29T15:21:07Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:00029002
2023-01-16T05:03:45Z
1903:1904:1905
Diastereoselective Methylation at the Congested β-Position of a Butenolide Ring: Studies toward the Synthesis of seco-Prezizaane-Type Sesquiterpenes
Kawamura, Tomoyoshi
Moriya, Hirokazu
Shibuya, Masatoshi
Yamamoto, Yoshihiko
open access
“This document is the Accepted Manuscript version of a Published Work that appeared in final form in [The Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-i5vuyRS94wFJb4GXufGB].”
We established a method for installing a methyl group at the β-position of a butenolide ring. The methylated position is located at the congested ring juncture of a 5,6,5-tricyclic lactone, which is common to neurotrophic seco-prezizaane-type sesquiterpenes. The samarium(II)-mediated conjugate addition of the halomethylsilyl ethers tethered to the proximal hydroxy groups efficiently formed the desired C–C bond. Subsequent fluoride-free Tamao oxidation and Barton–McCombie deoxygenation converted the resultant cyclic silyl ether into the corresponding methyl group.
ファイル公開:2020-10-04
ACS Publications
2019-10-04
eng
journal article
AM
http://hdl.handle.net/2237/00031189
https://nagoya.repo.nii.ac.jp/records/29002
https://doi.org/10.1021/acs.joc.9b02017
0022-3263
The Journal of Organic Chemistry
84
19
12508
12519
https://nagoya.repo.nii.ac.jp/record/29002/files/Manuscript.pdf
application/pdf
1.2 MB
2020-10-04