2024-03-28T19:36:37Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:02001506
2023-01-16T05:15:25Z
1903:1904:1905
Total Synthesis of Haliclonin A
Jin, Yuan
Orihara, Kensuke
Kawagishi, Fumiki
Toma, Tatsuya
Fukuyama, Tohru
Yokoshima, Satoshi
The total synthesis of haliclonin A was accomplished. Starting from 3,5-dimethoxybenzoic acid, a functionalized cyclohexanone fused to a 17-membered ring was prepared through a Birch reduction/alkylation sequence, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition of an organocopper reagent to an enone moiety. Reductive C−N bond formation via an N,O-acetal forged the 3-azabicyclo[3.3.1]nonane core. The allyl alcohol moiety was constructed by a sequence involving stereoselective α-selenylation of an aldehyde via an enamine, syn-elimination of a selenoxide, and allylation of the aldehyde with an allylboronate. Formation of the 15-membered ring containing a skipped diene was achieved by ring-closing metathesis, and final transformations led to the synthesis of haliclonin A.
journal article
Wiley
2021-04-19
application/pdf
Angewandte Chemie International Edition
17
60
9666
9671
1433-7851
https://nagoya.repo.nii.ac.jp/record/2001506/files/20210203_jin.pdf
eng
https://doi.org/10.1002/anie.202016343
"This is the peer reviewed version of the following article: [Y. Jin, K. Orihara, F. Kawagishi, T. Toma, T. Fukuyama, S. Yokoshima, Angew. Chem. Int. Ed. 2021, 60, 9666.], which has been published in final form at [https://doi.org/10.1002/anie.202016343]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited."