41049-30-3Relevant articles and documents
SYNTHESIS AND STRUCTURAL STUDIES OF BRIDGEHEAD DIENES 3-OXOBICYCLODODECA-1(11),8(9)-DIENE-(ZZ)-11-CARBOXYLIC ACID AND 3-OXOBICYCLOTRIDECA-1(12),9(10)-DIENE-(ZZ)-12-CARBOXYLIC ACID
Shea, K. J.,Burke, L. D.,Doedens, Robert J.
, p. 1841 - 1844 (1986)
Single crystal X-ray structures of two bridgehead dienes are reported.The bridgehead double bonds of diene 7 show only modest deviation from strain-free tetrasubstituted double bonds.The double bonds in bridgehead diene 6, however, exhibit an average deviation of the C-C=C-C torsion angle (Φ+Χ) of 14 deg.
Total Synthesis of Phenanthropiperidine Alkaloids by Sequential Alkylation of N,N-Dibenzylaminoacetonitrile
Bouvry, Christelle,Cupif, Jean-Fran?ois,Franzetti, Milène,Hurvois, Jean-Pierre
, p. 6037 - 6051 (2021/12/10)
Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as a substrate. This approach relies on the unprecedented condensation of metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected to a NaBH4-mediated reductive decyanation process to form homobenzylic amines. From these intermediates, a terminal leaving group was introduced by simple chemical manipulation, and its displacement by a free primary amine under two favorable cyclization processes led to the formation of the future E-ring of both alkaloids in high yields. Finally, a late Pictet-Spengler cyclization ensured the formation of a D-ring for the alkaloids 1 and 2.
Spiroacetal biosynthesis in fruit flies is complex: Distinguishable origins of the same major spiroacetal released by different Bactrocera spp.
Schwartz, Brett D.,Booth, Yvonne K.,Fletcher, Mary T.,Kitching, William,De Voss, James J.
supporting information; experimental part, p. 1526 - 1528 (2010/06/12)
The major spiroacetal ((E,E)-1) of the pestiferous fruit flies, Bactrocera tryoni and Bactrocera cucumis, is biosynthesised from fatty acids by distinguishable pathways which utilise modified β-oxidation and C-H hydroxylation, generating a putative ketodiol which cyclises. The Royal Society of Chemistry 2010.