| Full text | |
| 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: | 11/13993-2 - Methodologies for the synthesis of bioactive terpenes |
| Grantee: | Timothy John Brocksom |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 13/06532-4 - Cross-coupling reactions on the synthesis of new photosensitizers with high conjugation |
| Grantee: | Kleber Thiago de Oliveira |
| Support Opportunities: | 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 Opportunities: | Scholarships in Brazil - Doctorate |