118598-35-9Relevant academic research and scientific papers
Acetal-initiated Prins bicyclization for the synthesis of hexahydrofuro-[3,4-c]furan lignans and octahydropyrano[3,4-c]pyran derivatives
Subba Reddy,Ramana Reddy,Sridhar,Singarapu, Kiran Kumar
supporting information, p. 4754 - 4762 (2014/06/24)
An acetal-initiated Prins bicyclization approach has been developed for the stereoselective synthesis of hexahydrofuro[3,4-c]furan lignans. This also provides a direct way to generate a new series of octahydropyrano[3,4-c]pyran derivatives in a single-ste
A Short, Oxetane-Based Synthesis of (+/-)-Sarracenin
Hoye, Thomas R.,Richardson, Wendy S.
, p. 688 - 693 (2007/10/02)
(+/-)-Sarracenin (1) was synthesized in nine steps and six pots from simple precursors acetaldehyde and cyclopentadiene.Paterno-Buechi photocycloaddition of this pair yielded two diastereomeric oxetanes (3x, 3n).The major, exo isomer underwent highly regioselective acid-catalyzed methanolysis at the methyl-bearing oxetane center to give a 3-cyclopentenol derivative (8).Attachment of a methyl 2-(2-phenylethenyl)ethanoate moiety, a 3-oxopropanoate equivalent, with inversion of the toluenesulfonate 9 derived from 8 gave a diene (11) containing all of the necessary carbon atoms.Following decarbomethoxylation, both olefins were simultaneously ozonized to an in situ equivalent of trialdehyde (2) which has played a role in previous synthetic studies and biosynthetic postulates in this area.Spontaneous dehydration of 2 produced (+/-)-sarracenin in 18percent overall yield from the tosylate 9, the first purified intermediate in the sequence.
