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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

A practical deca-gram scale ring expansion of (R)-(-)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1

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Author(s):
Alves, Leandro de C. [1] ; Desidera, Andre L. [1] ; de Oliveira, Kleber T. [1] ; Newton, Sean [2] ; Ley, Steven V. [2] ; Brocksom, Timothy J. [1]
Total Authors: 6
Affiliation:
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW - England
Total Affiliations: 2
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 13, n. 28, p. 7633-7642, 2015.
Web of Science Citations: 7
Abstract

A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau-Demjanov reaction. Starting from readily available (R)-(-)-carvone, this robust sequence is available on a deca-gram scale and uses flow chemistry for the initial epoxidation reaction. The stereochemistry of the addition of two nucleophiles to the carbonyl group of (R)-(-)-carvone has been determined by X-ray diffraction studies and chemical correlation. (AU)

FAPESP's process: 13/06532-4 - Cross-coupling reactions on the synthesis of new photosensitizers with high conjugation
Grantee:Kleber Thiago de Oliveira
Support type: Regular Research Grants
FAPESP's process: 11/13993-2 - Methodologies for the synthesis of bioactive terpenes
Grantee:Timothy John Brocksom
Support type: Regular Research Grants
FAPESP's process: 14/12001-4 - The study of new guaianes, spiro and substituted benzenes derivatives from R-(-)-carvone and total synthesis in flow of spirodienal a and spirogien a methyl esther
Grantee:Leandro de Carvalho Alves
Support type: Scholarships in Brazil - Doctorate