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Total synthesis and preliminary biological evaluation of cis-solamin isomers

Total synthesis and preliminary biological evaluation of cis-solamin isomers
Total synthesis and preliminary biological evaluation of cis-solamin isomers
An efficient total synthesis of cis-solamin (1) has been achieved in 21% overall yield and with a longest linear sequence of just 11 steps from aldehyde S. A key feature of the approach was the use of asymmetric permanganate-promoted oxidative cyclization to introduce four of the five required stereocenters in a single step. The use of robust and chemoselective methodology meant that the use of protecting groups could be avoided during the assembly of cis-solamin (1) from the three fragments 23, 6, and 4. The methodology was also applied to the synthesis of three further cis-solamin isomers 2, ent-1, and ent-2. Cytotoxicity and hemolytic properties of cis-solamin isomers and synthetic intermediates are reported.
tetrahydrofuran-containing fragments, promoted oxidative cyclization, annonaceous acetogenins, stereoselective-synthesis, permanganateoxidation, modular synthesis, bioactive polyketides, rhenium(vii)oxides, natural-products, 1, 5-dienes
0022-3263
3368-3374
Cecil, Alex R.L.
85c727e5-86ae-4dd1-adfd-74671ffa213e
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Vicent, María J.
2402407c-9614-436f-85dc-e48b283f3fa5
Duncan, Ruth
a4281bc6-36f9-4056-82cf-130d10b2f77d
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Cecil, Alex R.L.
85c727e5-86ae-4dd1-adfd-74671ffa213e
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Vicent, María J.
2402407c-9614-436f-85dc-e48b283f3fa5
Duncan, Ruth
a4281bc6-36f9-4056-82cf-130d10b2f77d
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Cecil, Alex R.L., Hu, Yulai, Vicent, María J., Duncan, Ruth and Brown, Richard C.D. (2004) Total synthesis and preliminary biological evaluation of cis-solamin isomers. Journal of Organic Chemistry, 69 (10), 3368-3374. (doi:10.1021/jo049909g).

Record type: Article

Abstract

An efficient total synthesis of cis-solamin (1) has been achieved in 21% overall yield and with a longest linear sequence of just 11 steps from aldehyde S. A key feature of the approach was the use of asymmetric permanganate-promoted oxidative cyclization to introduce four of the five required stereocenters in a single step. The use of robust and chemoselective methodology meant that the use of protecting groups could be avoided during the assembly of cis-solamin (1) from the three fragments 23, 6, and 4. The methodology was also applied to the synthesis of three further cis-solamin isomers 2, ent-1, and ent-2. Cytotoxicity and hemolytic properties of cis-solamin isomers and synthetic intermediates are reported.

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More information

Published date: 14 May 2004
Keywords: tetrahydrofuran-containing fragments, promoted oxidative cyclization, annonaceous acetogenins, stereoselective-synthesis, permanganateoxidation, modular synthesis, bioactive polyketides, rhenium(vii)oxides, natural-products, 1, 5-dienes

Identifiers

Local EPrints ID: 20163
URI: https://eprints.soton.ac.uk/id/eprint/20163
ISSN: 0022-3263
PURE UUID: 3d50fabb-0c1d-45a7-979d-5b07ba80b84d
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 22 Feb 2006
Last modified: 06 Jun 2018 13:01

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