Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

Guangyan Du; Wenli Bao; Junrong Huang; Shuangping Huang; Hong Yue; Wei Yang; Lizhi Zhu; Zhenhao Liang; Chi Sing Lee

doi:10.1021/acs.orglett.5b00586

Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

Guangyan Du
, Wenli Bao
, Junrong Huang
, Shuangping Huang
, Hong Yue
, Wei Yang
, Lizhi Zhu
, Zhenhao Liang
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

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

10 Citations (Scopus)

Abstract

of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield.

Original language	English
Pages (from-to)	2062-2065
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	9
Early online date	10 Apr 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b00586
Publication status	Published - 1 May 2015

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10.1021/acs.orglett.5b00586

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title = "Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy",

abstract = "of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63\% yield.",

author = "Guangyan Du and Wenli Bao and Junrong Huang and Shuangping Huang and Hong Yue and Wei Yang and Lizhi Zhu and Zhenhao Liang and Lee, \{Chi Sing\}",

note = "We gratefully thank the NSFC (National Natural Science Foundation of China, Nos. 20972004 and 21272012), the SSTIC (Shenzhen Science and Technology Innovation Committee, KQTD201103 and ZDSY20120614144410389), Nanshan (KC2014ZDZJ0026A), and Peking University Shenzhen Graduate School for financial support. Publisher Copyright: {\textcopyright} 2015 American Chemical Society",

year = "2015",

month = may,

day = "1",

doi = "10.1021/acs.orglett.5b00586",

language = "English",

volume = "17",

pages = "2062--2065",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

AU - Du, Guangyan

AU - Bao, Wenli

AU - Huang, Junrong

AU - Huang, Shuangping

AU - Yue, Hong

AU - Yang, Wei

AU - Zhu, Lizhi

AU - Liang, Zhenhao

AU - Lee, Chi Sing

N1 - We gratefully thank the NSFC (National Natural Science Foundation of China, Nos. 20972004 and 21272012), the SSTIC (Shenzhen Science and Technology Innovation Committee, KQTD201103 and ZDSY20120614144410389), Nanshan (KC2014ZDZJ0026A), and Peking University Shenzhen Graduate School for financial support. Publisher Copyright: © 2015 American Chemical Society

PY - 2015/5/1

Y1 - 2015/5/1

N2 - of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield.

AB - of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield.

U2 - 10.1021/acs.orglett.5b00586

DO - 10.1021/acs.orglett.5b00586

M3 - Journal article

SN - 1523-7060

VL - 17

SP - 2062

EP - 2065

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

Abstract

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