4.8 Article

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

Journal

ORGANIC LETTERS
Volume 23, Issue 17, Pages 6642-6647

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02173

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Funding

  1. Council of Scientific and Industrial Research (CSIR), New Delhi [HCP0008]
  2. CSIR, New Delhi

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A reliable method for enone transposition using silyl group masking was developed. The method highlights enantio-switching, substituent shuffling, and Z-selectivity. It was successfully applied for the total synthesis of peribysin D and claimed for the formal synthesis of E-guggulsterone and E-volkendousin.
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.

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