84132-31-0Relevant academic research and scientific papers
SYNTHETIC STUDIES ON PYRROLIZIDINE ALKALOIDS. II. INTRAMOLECULAR ADDITIONS OF RADICALS AND ELECTROPHILES TO ALLYLSTANNANES AS METHODS FOR RING CLOSURE.
Keck, Gary E.,Enholm, Eric J.
, p. 3311 - 3314 (1985)
The simple pyrrolizidine alkaloid (+/-)-isoretronecanol was efficiently constructed by a route involving the attachment of an allylstannane moiety to succinimide followed by appropriate reduction, activation, and cyclization by either "one-electron" or "t
Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring: Via vinylogous C-N bond formation
Raghavan, Sadagopan,Ravi, Anil
, p. 10222 - 10229 (2016/11/17)
The synthesis of crinane is disclosed via intramolecular C-N bond formation by the displacement of an allylic sulfoxonium salt. The allylic sulfide precursor was synthesized by a ring-closing metathesis reaction. The quaternary carbon stereocenter was created by alkylation of a benzylic cyanide. The allyl sulfide 14 was prepared by adding vinylmagnesium bromide to an α-chlorosulfide.
AN EFFICIENT SYNTHETIC ROUTE TO γ,δ-UNSATURATED SEVEN-MEMBERED LACTONES
Kido, Fusao,Kazi, Abul B.,Yamaji, Kazuo,Kato, Michiharu,Yoshikoshi, Akira
, p. 607 - 618 (2007/10/02)
Treatment of the diazomalonates (9a-d) of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate resulted in the sigmatropic rearrangement of six-membered allylsulfonium ylides to provide γ,δ-unsaturated seven-membered lactones (10a-d) in
New Entry to γ,δ-Unsaturated Seven-membered Lactones
Kido, Fusao,Kazi, Abul B.,Yoshikoshi, Akira
, p. 613 - 616 (2007/10/02)
The sigmatropic rearrangement of cyclic allyl-sulfonium ylides, generated from the diazo malonates of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate, afforded γ,δ-unsaturated seven-membered lactones in moderate to good yields.
Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids
Keck, Gary E.,Cressman, Erik N. K.,Enholm, Eric J.
, p. 4345 - 4349 (2007/10/02)
Syntheses of (+/-)-isoretronecanol, (+/-)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed.The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction o
Quassinoids. 1. Attempted Intramolecular Diels-Alder Approach for Assembling the ABCD Rings
Voyle, Martyn,Kyler, Keith S.,Arseniyadis, Simeon,Dunlap, Norma K.,Watt, David S.
, p. 470 - 476 (2007/10/02)
A synthetic approach to the quassinoids involved the attempted intramolecular Diels-Alder reaction of the ester 31.The diene component, 4-(phenylthio)-3,5-hexadienoic acid (5) was prepared either by carboxylation of the anion of 3-(phenylthio)-1,3-pentadi
