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New approach to ?-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling

New approach to ?-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling
New approach to ?-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling
A short synthesis of unfunctionalized lactenediyne 3 by closure of the ten-membered ring at the double bond site is reported. After failure of the known methodologies, this closure was eventually successfully achieved thanks to a highly stereoselective, vanadium(II)-mediated pinacol coupling of bis(alk-2-ynal) 7.
enediynes, vanadium, pinacol coupling, macrocycles, lactams cyclic enediynes, dynemicin-a, conjugated enediynes, system, ring, 1, 2-diols, aldehydes, design, cycloaromatization, lactendiynes
1434-193X
939-946
Banfi, L.
b043b60a-712b-4cf0-ba40-0ad07626ed1c
Guanti, G.
0313997d-057b-43f9-a6b3-8e54ac3d44ee
Basso, A.
9cdcd616-ad0c-431a-b3f3-f39343a63694
Banfi, L.
b043b60a-712b-4cf0-ba40-0ad07626ed1c
Guanti, G.
0313997d-057b-43f9-a6b3-8e54ac3d44ee
Basso, A.
9cdcd616-ad0c-431a-b3f3-f39343a63694

Banfi, L., Guanti, G. and Basso, A. (2000) New approach to ?-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling. European Journal of Organic Chemistry, (6), 939-946. (doi:10.1002/(SICI)1099-0690(200003)2000:6<939::AID-EJOC939>3.0.CO;2-Q).

Record type: Article

Abstract

A short synthesis of unfunctionalized lactenediyne 3 by closure of the ten-membered ring at the double bond site is reported. After failure of the known methodologies, this closure was eventually successfully achieved thanks to a highly stereoselective, vanadium(II)-mediated pinacol coupling of bis(alk-2-ynal) 7.

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More information

Published date: 1 March 2000
Keywords: enediynes, vanadium, pinacol coupling, macrocycles, lactams cyclic enediynes, dynemicin-a, conjugated enediynes, system, ring, 1, 2-diols, aldehydes, design, cycloaromatization, lactendiynes

Identifiers

Local EPrints ID: 18954
URI: https://eprints.soton.ac.uk/id/eprint/18954
ISSN: 1434-193X
PURE UUID: a2eb6178-28c9-42b3-9c19-83d43e3144a0

Catalogue record

Date deposited: 18 Jan 2006
Last modified: 17 Jul 2017 16:34

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