Organic Letters

, volume 23 , issue 17 , pages 6642-6647

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

Paresh R Athawale ^{1, 2}

Vishal M Zade ^{1, 2}

Gamidi Rama Krishna ¹

Dumbala Srinivasa Reddy ^{1, 2, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India |

Academy of Scientific and innovative Research (AcSIR), Ghaziabad 201002, India |

CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India |

Publication type: Journal Article

Publication date: 2021-08-13

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c02173

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PubMed ID: 34387997

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

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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Athawale P. R. et al. Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone // Organic Letters. 2021. Vol. 23. No. 17. pp. 6642-6647.

GOST all authors (up to 50) Copy

Athawale P. R., Zade V. M., Rama Krishna G., Reddy D. S. Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone // Organic Letters. 2021. Vol. 23. No. 17. pp. 6642-6647.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.1c02173

UR - https://doi.org/10.1021/acs.orglett.1c02173

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

T2 - Organic Letters

AU - Athawale, Paresh R

AU - Zade, Vishal M

AU - Rama Krishna, Gamidi

AU - Reddy, Dumbala Srinivasa

PY - 2021

DA - 2021/08/13

PB - American Chemical Society (ACS)

SP - 6642-6647

IS - 17

VL - 23

PMID - 34387997

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Athawale,

author = {Paresh R Athawale and Vishal M Zade and Gamidi Rama Krishna and Dumbala Srinivasa Reddy},

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

journal = {Organic Letters},

year = {2021},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.orglett.1c02173},

number = {17},

pages = {6642--6647},

doi = {10.1021/acs.orglett.1c02173}

}

MLA

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MLA Copy

Athawale, Paresh R., et al. “Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone.” Organic Letters, vol. 23, no. 17, Aug. 2021, pp. 6642-6647. https://doi.org/10.1021/acs.orglett.1c02173.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)