10236-06-3Relevant articles and documents
Efficient photochemical synthesis of 2-vinylcyclopropanecarbaldehydes, precursors of cyclopropane components present in pyrethroids, by using the oxa-di-π-methane rearrangement
Armesto, Diego,Ortiz, Maria J.,Agarrabeitia, Antonia R.,El-Boulifi, Noureddin
experimental part, p. 8690 - 8697 (2011/01/04)
A comparative study on the triplet photoreactivity of a series of β,γ,δ,ε-unsaturated aldehydes 14a-f and 15, using 3-methoxyacetophenone and 4-phenylbenzophenone as sensitizers, has been carried out. When 3-methoxyacetophenone is used as the triplet sensitizer, the aldehydes undergo oxa-di-π-methane rearrangement (ODPM) to afford the corresponding cyclopropanecarbaldehydes 16a-f and 17 in yields ranging from 14% to 62% in addition in most cases to products resulting from decarbonylation. However, when 4-phenylbenzophenone is used as the photosensitizer ODPM products are obtained exclusively in almost quantitative yield. These are additional examples of the recently described, unexpected influence of the nature of the triplet sensitizer on the photoreactivity of organic compounds.
The Synthesis of Two Furan-Based Analogues of the α′,β ′-Epoxy Ketone Proteasome Inhibitor Eponemycin
Bennacer, Bibia,Trubuil, Dominique,Rivalle, Christian,Grierson, David S.
, p. 4561 - 4568 (2007/10/03)
Myers's methodology for enantioselective amino acid synthesis was employed to prepare the N-Boc didehydroleucine amide derivative 15 and to effect its conversion into the acylfuran intermediate 17. Coupling of 19 (R = H) with N-(isooctanoyl)serine provided the furan-based analogue 4 of eponemycin (de = 96 %), a peptide epoxide with potent cytotoxic and anti-angiogenesis properties. In an identical fashion the corresponding unsaturated analogue 5 of eponemycin was prepared (de = 48%). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Synthesis of functionalized bicycloocta-2,6-dienes by thermal rearrangement of substituted 6-exo-(1-alkenyl)bicyclohex-2-ene systems
Piers, Edward,Jung, Grace L.,Ruediger, Edward H.
, p. 670 - 682 (2007/10/02)
Thermolysis of each of the enol silyl ethers 31-35 affords, cleanly and efficiently, the bicyclooctadienes 36-40, respectively.Similarly, thermal rearrangement of the enol silyl ether 50 provides the diene 51.Hydrolysis of 36, 37, and 39, and decar
