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Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization

Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization
Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization
cis-Solamin (1) and its diastereoisomer 14 have been synthesized in 13 steps using the diastereoselective permanganate-promoted oxidative cyclization of 1,5-dienes to create the tetrahydrofuran diol core. Notably, no protecting groups are required during the stages of fragment assembly.
annonaceous acetogenins, stereoselective synthesis, 1, 5-dienes, polycyclization, (+)-parviflorin, asimicin
1523-7060
3715-3718
Cecil, Alexander R.L.
fe27fc16-a629-488d-a09f-c7c2a9d9f64e
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Cecil, Alexander R.L.
fe27fc16-a629-488d-a09f-c7c2a9d9f64e
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Cecil, Alexander R.L. and Brown, Richard C.D. (2002) Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization. Organic Letters, 4 (21), 3715-3718. (doi:10.1021/ol026669n).

Record type: Article

Abstract

cis-Solamin (1) and its diastereoisomer 14 have been synthesized in 13 steps using the diastereoselective permanganate-promoted oxidative cyclization of 1,5-dienes to create the tetrahydrofuran diol core. Notably, no protecting groups are required during the stages of fragment assembly.

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More information

Published date: 2002
Keywords: annonaceous acetogenins, stereoselective synthesis, 1, 5-dienes, polycyclization, (+)-parviflorin, asimicin

Identifiers

Local EPrints ID: 19695
URI: http://eprints.soton.ac.uk/id/eprint/19695
ISSN: 1523-7060
PURE UUID: 8fa1f2fd-213c-45f9-b1ef-0150e6745328
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 16 Feb 2006
Last modified: 29 Oct 2019 02:03

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