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A short diastereoselective total synthesis of (±)-vibralactone

A short diastereoselective total synthesis of (±)-vibralactone
A short diastereoselective total synthesis of (±)-vibralactone
A total synthesis of the (±)-vibralactone has been achieved in 11 steps and 16% overall yield from malonic acid. Key steps include a highly diastereoselective allylation of an α-formyl ester containing an all carbon α-quaternary center, a Pd-catalyzed deallylative β-lactonization, and an aldehyde-selective Wacker oxidation of a terminal alkene.
1523-7060
5971-5973
Leeder, Alexander J.
eb778e32-652e-45d5-8f3d-259928c2d0cf
Heap, Robert J.
c1557a74-f91f-4a3d-8767-23abe717065c
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Franck, Xavier
1febe887-06d8-4ae5-bd8b-cebf1663b14a
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Leeder, Alexander J.
eb778e32-652e-45d5-8f3d-259928c2d0cf
Heap, Robert J.
c1557a74-f91f-4a3d-8767-23abe717065c
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Franck, Xavier
1febe887-06d8-4ae5-bd8b-cebf1663b14a
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Leeder, Alexander J., Heap, Robert J., Brown, Lynda J., Franck, Xavier and Brown, Richard C. D. (2016) A short diastereoselective total synthesis of (±)-vibralactone. Organic Letters, 18 (23), 5971-5973. (doi:10.1021/acs.orglett.6b03007).

Record type: Article

Abstract

A total synthesis of the (±)-vibralactone has been achieved in 11 steps and 16% overall yield from malonic acid. Key steps include a highly diastereoselective allylation of an α-formyl ester containing an all carbon α-quaternary center, a Pd-catalyzed deallylative β-lactonization, and an aldehyde-selective Wacker oxidation of a terminal alkene.

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More information

Accepted/In Press date: 28 October 2016
e-pub ahead of print date: 31 October 2016
Published date: 2 December 2016
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 402837
URI: http://eprints.soton.ac.uk/id/eprint/402837
DOI: doi:10.1021/acs.orglett.6b03007
ISSN: 1523-7060
PURE UUID: d0567f7f-351f-4d20-a5e8-46bd12bf7323
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Richard C. D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 17 Nov 2016 12:46
Last modified: 16 Mar 2024 03:00

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Contributors

Author: Alexander J. Leeder
Author: Robert J. Heap
Author: Lynda J. Brown ORCID iD
Author: Xavier Franck
Author: Richard C. D. Brown ORCID iD

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