Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene

Nicholas A. Clanton; Nicolas A. Wilson; Eliezer Ortiz; Shawn T. Blumberg; Doug E. Frantz

doi:10.1021/acs.orglett.2c04145

Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene

Nicholas A. Clanton
, Nicolas A. Wilson
, Eliezer Ortiz
, Shawn T. Blumberg
, Doug E. Frantz

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

The site-selective functionalization of unactivated allylic C-H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is shown with further extrapolation to the first large-scale telescoped chemical synthesis of artemisinic acid from amorphadiene. Finally, application of the method for the successful site-selective functionalization of unactivated allylic C-H bonds in other terpene-based natural products is also highlighted.

Original language	English
Pages (from-to)	277-281
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.2c04145
State	Published - Jan 13 2023

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10.1021/acs.orglett.2c04145

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title = "Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene",

abstract = "The site-selective functionalization of unactivated allylic C-H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is shown with further extrapolation to the first large-scale telescoped chemical synthesis of artemisinic acid from amorphadiene. Finally, application of the method for the successful site-selective functionalization of unactivated allylic C-H bonds in other terpene-based natural products is also highlighted.",

author = "Clanton, \{Nicholas A.\} and Wilson, \{Nicolas A.\} and Eliezer Ortiz and Blumberg, \{Shawn T.\} and Frantz, \{Doug E.\}",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

month = jan,

day = "13",

doi = "10.1021/acs.orglett.2c04145",

language = "English",

volume = "25",

pages = "277--281",

journal = "Organic Letters",

issn = "1523-7060",

number = "1",

}

Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene. / Clanton, Nicholas A.; Wilson, Nicolas A.; Ortiz, Eliezer et al.
In: Organic Letters, Vol. 25, No. 1, 13.01.2023, p. 277-281.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP

T2 - Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene

AU - Clanton, Nicholas A.

AU - Wilson, Nicolas A.

AU - Ortiz, Eliezer

AU - Blumberg, Shawn T.

AU - Frantz, Doug E.

PY - 2023/1/13

Y1 - 2023/1/13

N2 - The site-selective functionalization of unactivated allylic C-H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is shown with further extrapolation to the first large-scale telescoped chemical synthesis of artemisinic acid from amorphadiene. Finally, application of the method for the successful site-selective functionalization of unactivated allylic C-H bonds in other terpene-based natural products is also highlighted.

AB - The site-selective functionalization of unactivated allylic C-H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is shown with further extrapolation to the first large-scale telescoped chemical synthesis of artemisinic acid from amorphadiene. Finally, application of the method for the successful site-selective functionalization of unactivated allylic C-H bonds in other terpene-based natural products is also highlighted.

UR - https://www.scopus.com/pages/publications/85146033711

U2 - 10.1021/acs.orglett.2c04145

DO - 10.1021/acs.orglett.2c04145

M3 - Article

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SN - 1523-7060

VL - 25

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EP - 281

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene

Abstract

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