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Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation

Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation
Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation
A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C-2 Symmetrical (Z,E,E,Z)-and (E,E,E,E)-tetraenes 5 and 6 were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene 5 was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrisation of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.
1477-0520
1017-1024
Bhunnoo, Riaz A.
3cbd0ce5-3d94-4ad9-a793-5a6ec8acd63c
Hobbs, Heather
2cba3887-fe3f-48e9-abb8-046b31b92c87
Laine, Dramane I.
ada06dad-a37e-4e30-950c-c8413cc4b0f6
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Bhunnoo, Riaz A.
3cbd0ce5-3d94-4ad9-a793-5a6ec8acd63c
Hobbs, Heather
2cba3887-fe3f-48e9-abb8-046b31b92c87
Laine, Dramane I.
ada06dad-a37e-4e30-950c-c8413cc4b0f6
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Bhunnoo, Riaz A., Hobbs, Heather, Laine, Dramane I., Light, Mark Edward and Brown, Richard C. D. (2009) Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation. Organic & Biomolecular Chemistry, 7 (5), 1017-1024. (doi:10.1039/b813201a).

Record type: Article

Abstract

A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C-2 Symmetrical (Z,E,E,Z)-and (E,E,E,E)-tetraenes 5 and 6 were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene 5 was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrisation of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.

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More information

Published date: 2009

Identifiers

Local EPrints ID: 67655
URI: https://eprints.soton.ac.uk/id/eprint/67655
ISSN: 1477-0520
PURE UUID: f18f3386-c04b-4537-bc61-b5fbdf70ca2f
ORCID for Mark Edward Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Richard C. D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 02 Sep 2009
Last modified: 20 Jul 2019 01:16

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