Bioinspired Total Synthesis of (±)-Yezo’otogirin C

Shuzhong He; Wei Yang; Lizhi Zhu; Guangyan Du; Chi Sing Lee

doi:10.1021/ol403374h

Bioinspired Total Synthesis of (±)-Yezo’otogirin C

Shuzhong He
, Wei Yang
, Lizhi Zhu
, Guangyan Du
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

35 Citations (Scopus)

Abstract

The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.

Original language	English
Pages (from-to)	496-499
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	2
Early online date	30 Dec 2013
DOIs	https://doi.org/10.1021/ol403374h
Publication status	Published - 17 Jan 2014

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@article{52a598166eb248b392058f93b6180861,

title = "Bioinspired Total Synthesis of (±)-Yezo{\textquoteright}otogirin C",

abstract = "The first and protective group-free total synthesis of (±)-yezo{\textquoteright}otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23\% overall yield. The tricyclic core of (±)-yezo{\textquoteright}otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.",

author = "Shuzhong He and Wei Yang and Lizhi Zhu and Guangyan Du and Lee, \{Chi Sing\}",

note = "This work is supported by the National Natural Science Foundation of China (Grant No. 21072008) and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Prof. Tao Wang (Peking University Shenzhen Graduate School) for the X-ray crystallography of compound 13. Publisher Copyright: {\textcopyright} 2013 American Chemical Society",

year = "2014",

month = jan,

day = "17",

doi = "10.1021/ol403374h",

language = "English",

volume = "16",

pages = "496--499",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Bioinspired Total Synthesis of (±)-Yezo’otogirin C

AU - He, Shuzhong

AU - Yang, Wei

AU - Zhu, Lizhi

AU - Du, Guangyan

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (Grant No. 21072008) and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Prof. Tao Wang (Peking University Shenzhen Graduate School) for the X-ray crystallography of compound 13. Publisher Copyright: © 2013 American Chemical Society

PY - 2014/1/17

Y1 - 2014/1/17

N2 - The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.

AB - The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.

U2 - 10.1021/ol403374h

DO - 10.1021/ol403374h

M3 - Journal article

SN - 1523-7060

VL - 16

SP - 496

EP - 499

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Bioinspired Total Synthesis of (±)-Yezo’otogirin C

Abstract

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