820-25-7Relevant academic research and scientific papers
Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone
Athawale, Paresh R.,Zade, Vishal M.,Rama Krishna, Gamidi,Reddy, D. Srinivasa
supporting information, p. 6642 - 6647 (2021/09/02)
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.
New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum)
Naef, Regula,Velluz, Alain,Jaquier, Alain
experimental part, p. 517 - 527 (2009/04/10)
An extract of red bell peppers (Capsicum annuum) was prepared by simultaneous distillation-extraction (SDE, Likens-Nickerson). In addition to the already known (3E)-hepten-2-one (1), the unsaturated C9-ketones 1-nonen-4-one (2), (2E)-2-nonen-4-one (3), and (2E,5E)-2,5-nonadien-4-one (4), 2-methoxy-3-isobutylpyrazine (5), and heptane-2-thiol (6), we identified 19 new thiols (the aliphatic saturated and unsaturated thiols 14-16, and 22-27, the mercapto-ketones 12 and 13, the mercapto-alcohols 17, 18, and 30, the dithiols 19 and 28, the methylthio-thiols 20 and 21, and the thiophene-thiol 31) and the two new dithiolanes 10 and 29. All of them are structurally related to the unsaturated C7-and C9-ketones 1-4. The free thiols were enriched using Affi-Gel 501 (p-aminophenyl-mercuric acetate grafted on an agarose gel). The new compounds were confirmed by syntheses and were organoleptically evaluated.
Telluride-mediated stereospecific conversion of racemic E-allylic alcohols to homochiral Z-allylic alcohols; transposition of primary and secondary allylic alcohols via glycidol derivatives
Discordia, Robert P.,Murphy, Christopher K.,Dittmer, Donald C.
, p. 5603 - 5606 (2007/10/02)
Racemic trans-secondary allylic alcohols can be converted to homochiral cis-secondary allylic alcohols by means of a telluride-mediated transposition reaction applied to the homochiral glycidol obtained from a Sharpless kinetic resolution. (+)-Linalool is obtained in>95% enantiomeric excess from geraniol, an example of a transposition of a primary allylic alcohol to a homochiral tertiary alcohol.
Synthesis with sulfones, Part XLIII. Preparation of γ-functionalized vinyl sulfones by nucleophilic substitution of allylidene disulfones; stereospecific reduction of 3-hydroxy-(E)-1-propenyl sulfones to (Z)-allylic alcohols
Cuvigny, T.,Penhoat, C. Herve du,Julia, M.
, p. 409 - 421 (2007/10/02)
The substitution of a sulfonyl moiety ao allylidene disulfones by various nucleophiles (PhSNa, PhSO2Na, H2O and R2NH) leads to γ-functionalized (E)-vinyl sulfones.The stereospecific reduction of 3-hydroxy-(E)-1-propenyl sulfones affords (Z)-allylic alcoho
