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Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (±)-goniomitine.
Chemistry. 2014 Sep 26; 20(40):12768-72.C

Abstract

A Rh(III)-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway. Furthermore, using the Rh(III)-catalyzed C-H activation/annulation as a key step, a one-pot synthesis of pyrido[1,2-a]indoles has also been developed and applied to a highly efficient formal total synthesis of (±)-goniomitine.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou B
Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203 (P. R. China). zhoubing2012@hotmail.com.
Du J
No affiliation info available
Yang Y
No affiliation info available
Li Y
No affiliation info available

MeSH

AlkynesBiological ProductsCatalysisIndole AlkaloidsOxidation-ReductionRhodiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25145612

Citation

Zhou, Bing, et al. "Rhodium(III)-catalyzed Intramolecular Redox-neutral Annulation of Tethered Alkynes: Formal Total Synthesis of (±)-goniomitine." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 40, 2014, pp. 12768-72.
Zhou B, Du J, Yang Y, et al. Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (±)-goniomitine. Chemistry. 2014;20(40):12768-72.
Zhou, B., Du, J., Yang, Y., & Li, Y. (2014). Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (±)-goniomitine. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(40), 12768-72. https://doi.org/10.1002/chem.201403973
Zhou B, et al. Rhodium(III)-catalyzed Intramolecular Redox-neutral Annulation of Tethered Alkynes: Formal Total Synthesis of (±)-goniomitine. Chemistry. 2014 Sep 26;20(40):12768-72. PubMed PMID: 25145612.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (±)-goniomitine. AU - Zhou,Bing, AU - Du,Juanjuan, AU - Yang,Yaxi, AU - Li,Yuanchao, Y1 - 2014/08/21/ PY - 2014/06/15/received PY - 2014/8/23/entrez PY - 2014/8/26/pubmed PY - 2015/6/3/medline KW - CH activation KW - goniomitine KW - indoles KW - redox-neutral KW - total synthesis SP - 12768 EP - 72 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 40 N2 - A Rh(III)-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway. Furthermore, using the Rh(III)-catalyzed C-H activation/annulation as a key step, a one-pot synthesis of pyrido[1,2-a]indoles has also been developed and applied to a highly efficient formal total synthesis of (±)-goniomitine. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25145612/Rhodium_III__catalyzed_intramolecular_redox_neutral_annulation_of_tethered_alkynes:_formal_total_synthesis_of__±__goniomitine_ DB - PRIME DP - Unbound Medicine ER -