Tags

Type your tag names separated by a space and hit enter

Total Synthesis of (±)-Integrifolin.
Chemistry. 2016 Jul 11; 22(29):9953-7.C

Abstract

The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Shimomaki K
Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan.
Kusama H
Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan. Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.
Iwasawa N
Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan. niwasawa@chem.titech.ac.jp.

MeSH

AlkenesCatalysisCyclizationEthersMolecular StructureOxidation-Reduction

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27147582

Citation

Shimomaki, Katsuya, et al. "Total Synthesis of (±)-Integrifolin." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 22, no. 29, 2016, pp. 9953-7.
Shimomaki K, Kusama H, Iwasawa N. Total Synthesis of (±)-Integrifolin. Chemistry. 2016;22(29):9953-7.
Shimomaki, K., Kusama, H., & Iwasawa, N. (2016). Total Synthesis of (±)-Integrifolin. Chemistry (Weinheim an Der Bergstrasse, Germany), 22(29), 9953-7. https://doi.org/10.1002/chem.201601275
Shimomaki K, Kusama H, Iwasawa N. Total Synthesis of (±)-Integrifolin. Chemistry. 2016 Jul 11;22(29):9953-7. PubMed PMID: 27147582.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total Synthesis of (±)-Integrifolin. AU - Shimomaki,Katsuya, AU - Kusama,Hiroyuki, AU - Iwasawa,Nobuharu, Y1 - 2016/06/13/ PY - 2016/03/17/received PY - 2016/5/6/entrez PY - 2016/5/6/pubmed PY - 2018/5/11/medline KW - alkenes KW - cyclization KW - sesquiterpenoids KW - total synthesis KW - tungsten SP - 9953 EP - 7 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 22 IS - 29 N2 - The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/27147582/Total_Synthesis_of__±__Integrifolin_ DB - PRIME DP - Unbound Medicine ER -