A concise synthesis of marine natural product (−)-15-oxopuupehenol from (+)-sclarelide

Yun Fei Cheng; Hui Jing Li; Yin Lin Zhang; Yan Chao Wu

doi:10.1080/14786419.2021.2000983

A concise synthesis of marine natural product (−)-15-oxopuupehenol from (+)-sclarelide

Yun Fei Cheng
, Hui Jing Li
, Yin Lin Zhang
, Yan Chao Wu^*

^*Corresponding author for this work

Harbin Institute of Technology Weihai
Ltd.

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

3 Scopus citations

Abstract

A step-economical synthesis of (−)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (−)-15-oxopuupehenol.

Original language	English
Pages (from-to)	1265-1270
Number of pages	6
Journal	Natural Product Research
Volume	37
Issue number	8
DOIs	https://doi.org/10.1080/14786419.2021.2000983
State	Published - 2023
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

(+)-sclarelide
(−)-15-oxopuupehenol
Marine natural product
step-economical synthesis

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10.1080/14786419.2021.2000983

Cite this

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title = "A concise synthesis of marine natural product (−)-15-oxopuupehenol from (+)-sclarelide",

abstract = "A step-economical synthesis of (−)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3\% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (−)-15-oxopuupehenol.",

keywords = "(+)-sclarelide, (−)-15-oxopuupehenol, Marine natural product, step-economical synthesis",

author = "Cheng, \{Yun Fei\} and Li, \{Hui Jing\} and Zhang, \{Yin Lin\} and Wu, \{Yan Chao\}",

note = "Publisher Copyright: {\textcopyright} 2021 Informa UK Limited, trading as Taylor \& Francis Group.",

year = "2023",

doi = "10.1080/14786419.2021.2000983",

language = "英语",

volume = "37",

pages = "1265--1270",

journal = "Natural Product Research",

issn = "1478-6419",

publisher = "Taylor and Francis Ltd.",

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}

TY - JOUR

T1 - A concise synthesis of marine natural product (−)-15-oxopuupehenol from (+)-sclarelide

AU - Cheng, Yun Fei

AU - Li, Hui Jing

AU - Zhang, Yin Lin

AU - Wu, Yan Chao

PY - 2023

Y1 - 2023

N2 - A step-economical synthesis of (−)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (−)-15-oxopuupehenol.

AB - A step-economical synthesis of (−)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (−)-15-oxopuupehenol.

KW - (+)-sclarelide

KW - (−)-15-oxopuupehenol

KW - Marine natural product

KW - step-economical synthesis

UR - https://www.scopus.com/pages/publications/85118532367

U2 - 10.1080/14786419.2021.2000983

DO - 10.1080/14786419.2021.2000983

M3 - 文章

C2 - 34727810

AN - SCOPUS:85118532367

SN - 1478-6419

VL - 37

SP - 1265

EP - 1270

JO - Natural Product Research

JF - Natural Product Research

IS - 8

ER -

A concise synthesis of marine natural product (−)-15-oxopuupehenol from (+)-sclarelide

Abstract

UN SDGs

Keywords

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