Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone
A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.
Athawale, Paresh R.,Zade, Vishal M.,Rama Krishna, Gamidi,Reddy, D. Srinivasa
p. 6642 - 6647
(2021/09/02)
THE ACID INDUCED DECOMPOSITION OF 7-SUBSTITUTED 3-DIAZO-2-NORBORNANONES.THE STRUCTURES OF THE PRODUCTS AND THEIR DISTRIBUTION
Introduction of a syn-7 isopropyl or t-butyl substituent in 3-diazo-2-norbornanone results in both endo and exo protonation in aqueous acid and a marked decrease in α-ketol and increase in tricyclanone formation.
Yates, Peter,Kronis, John D.
p. 2419 - 2422
(2007/10/02)
Four-Carbon Photochemical Annelation of Alkenes with 2,2,6-Trimethyl-1,3-dioxolenone
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Baldwin, S. W.,Wilkinson, J. M.
p. 3634 - 3635
(2007/10/02)
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