A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations

Taher, Abu; Aderibigbe, Blessing A; Morgans, Garreth L; Madeley, Lee G; Khanye, Setshaba D; Van der Westhuizen, Leandi; Fernandes, Manuel A; Smith, Vincent J; Michael, Joseph P; Green, Ivan R; Van Otterlo, Willem A L

Title: A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations
Creator: Taher, Abu
Creator: Aderibigbe, Blessing A
Creator: Morgans, Garreth L
Creator: Madeley, Lee G
Creator: Khanye, Setshaba D
Creator: Van der Westhuizen, Leandi
Creator: Fernandes, Manuel A
Creator: Smith, Vincent J
Creator: Michael, Joseph P
Creator: Green, Ivan R
Creator: Van Otterlo, Willem A L
Date Issued: 2013
Date: 2013
Type: text
Type: article
Identifier: http://hdl.handle.net/10962/66252
Identifier: vital:28925
Identifier: https://doi.org/10.1016/j.tet.2012.12.043
Description: publisher version
Description: A set of eight-membered benzannelated heterocycles containing two heteroatoms (O,O, NR,NR and O,NR where R=protecting group) was synthesized by ring-closing metathesis from the corresponding ortho-bis-allyl precursors. In this manner, 7-methoxy-2,5-dihydro-1,6-benzodioxocine, 1,2,5,6-tetrahydro-1,6-benzodiazocines, 5,6-dihydro-2H-1,6-benzoxazocines and 5,6,9,10-tetrahydropyrido[2,3-b][1,4]diazocine were synthesized. A number of these compounds were then treated with the catalyst [RuClH(CO)(PPh3)3] to facilitate isomerization of the alkene into conjugation with the heteroatoms in the eight-membered ring. Quite surprisingly, an equal ratio of regioisomers was obtained, even if the heteroatoms were different.
Format: 10 pages
Format: pdf
Language: English
Relation: Tetrahedron
Relation: Taher, Abu, Aderibigbe, Blessing A., Morgans, Garreth L., Madeley, Lee G., Khanye, Setshaba D., Van der Westhuizen, Leandi, Fernandes, Manuel A., Smith, Vincent J., Michael, Joseph P., Green, Ivan R., Van Otterlo, Willem A.L. (2013) A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations. Tetrahedron, 69 (8). p. 2038 – 2047. ISSN:0040-4020. https://doi.org/10.1016/j.tet.2012.12.043
Relation: Tetrahedron volume 69 number 2038 2047 88 February 2013 0040-4020
Rights: Elsevier B.V.
Rights: Use of this resource is governed by the terms and conditions of the Tetrahedron Open Access Options Statement (https://www.elsevier.com/journals/tetrahedron/0040-4020/open-access-options)

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Khanye, David Setshaba (Associate Prof)

RU Department of Chemistry

RU Department of Pharmacy

SDG 03. Good Health and Well-Being

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