Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane

Christopher J.J. Hall; Indi S. Marriott; Kirsten E. Christensen; Aaron J. Day; William R.F. Goundry; Timothy J. Donohoe

doi:10.1039/d2cc01248k

Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane

Christopher J.J. Hall
, Indi S. Marriott
, Kirsten E. Christensen
, Aaron J. Day
, William R.F. Goundry
, Timothy J. Donohoe

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

10 Citations (Scopus)

Abstract

The total synthesis of (-)-γ-lycorane (10 steps) and synthesis of (±)-γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* (Me₅C₆) deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project.

Original language	English
Pages (from-to)	4966-4968
Number of pages	3
Journal	Chemical Communications
Volume	58
Issue number	32
DOIs	https://doi.org/10.1039/d2cc01248k
Publication status	Published - 25 Apr 2022
Externally published	Yes

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10.1039/d2cc01248kLicence: CC BY

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title = "Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane",

abstract = "The total synthesis of (-)-γ-lycorane (10 steps) and synthesis of (±)-γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* (Me5C6) deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project.",

author = "Hall, \{Christopher J.J.\} and Marriott, \{Indi S.\} and Christensen, \{Kirsten E.\} and Day, \{Aaron J.\} and Goundry, \{William R.F.\} and Donohoe, \{Timothy J.\}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry",

year = "2022",

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day = "25",

doi = "10.1039/d2cc01248k",

language = "English",

volume = "58",

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TY - JOUR

T1 - Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane

AU - Hall, Christopher J.J.

AU - Marriott, Indi S.

AU - Christensen, Kirsten E.

AU - Day, Aaron J.

AU - Goundry, William R.F.

AU - Donohoe, Timothy J.

PY - 2022/4/25

Y1 - 2022/4/25

N2 - The total synthesis of (-)-γ-lycorane (10 steps) and synthesis of (±)-γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* (Me5C6) deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project.

AB - The total synthesis of (-)-γ-lycorane (10 steps) and synthesis of (±)-γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* (Me5C6) deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project.

UR - https://www.scopus.com/pages/publications/85128200887

U2 - 10.1039/d2cc01248k

DO - 10.1039/d2cc01248k

M3 - Article

C2 - 35348143

AN - SCOPUS:85128200887

SN - 1359-7345

VL - 58

SP - 4966

EP - 4968

JO - Chemical Communications

JF - Chemical Communications

IS - 32

ER -

Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane

Abstract

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