Asymmetric synthesis of Anomala Osakana Pheromone isomer using protecting group free strategy

Li Lin; A. Ni Li; Qing Yang Zhao; Fan Zhi Yang; Wen Yin; Rui Wang

doi:10.1007/s11434-010-3155-y

Asymmetric synthesis of Anomala Osakana Pheromone isomer using protecting group free strategy

Li Lin
, A. Ni Li
, Qing Yang Zhao
, Fan Zhi Yang
, Wen Yin
, Rui Wang^*

^*Corresponding author for this work

Lanzhou University

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

2 Citations (Scopus)

Abstract

The protecting group free synthesis of Anomala Osakana Pheromone isomer has been achieved with high enantioselectivity (92% ee). A chiral γ-hydroxy-α, β-acetylenic ester was used as the key intermediate, which was obtained via asymmetric alkynylation of aldehyde. This was followed by readily handled selective hydrogenation and lactonization in three steps with a high overall yield (86%).

Original language	English
Pages (from-to)	2811-2813
Number of pages	3
Journal	Chinese Science Bulletin
Volume	55
Issue number	25
DOIs	https://doi.org/10.1007/s11434-010-3155-y
Publication status	Published - 2010
Externally published	Yes

Keywords

asymmetric alkynylation
chiral γ-butyrolactone
swern oxidation
total synthesis
β-acetylenic ester
γ-hydroxy-α

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10.1007/s11434-010-3155-y

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title = "Asymmetric synthesis of Anomala Osakana Pheromone isomer using protecting group free strategy",

abstract = "The protecting group free synthesis of Anomala Osakana Pheromone isomer has been achieved with high enantioselectivity (92\% ee). A chiral γ-hydroxy-α, β-acetylenic ester was used as the key intermediate, which was obtained via asymmetric alkynylation of aldehyde. This was followed by readily handled selective hydrogenation and lactonization in three steps with a high overall yield (86\%).",

keywords = "asymmetric alkynylation, chiral γ-butyrolactone, swern oxidation, total synthesis, β-acetylenic ester, γ-hydroxy-α",

author = "Li Lin and Li, \{A. Ni\} and Zhao, \{Qing Yang\} and Yang, \{Fan Zhi\} and Wen Yin and Rui Wang",

year = "2010",

doi = "10.1007/s11434-010-3155-y",

language = "English",

volume = "55",

pages = "2811--2813",

journal = "Chinese Science Bulletin",

issn = "1001-6538",

publisher = "Science Press",

number = "25",

}

TY - JOUR

T1 - Asymmetric synthesis of Anomala Osakana Pheromone isomer using protecting group free strategy

AU - Lin, Li

AU - Li, A. Ni

AU - Zhao, Qing Yang

AU - Yang, Fan Zhi

AU - Yin, Wen

AU - Wang, Rui

PY - 2010

Y1 - 2010

N2 - The protecting group free synthesis of Anomala Osakana Pheromone isomer has been achieved with high enantioselectivity (92% ee). A chiral γ-hydroxy-α, β-acetylenic ester was used as the key intermediate, which was obtained via asymmetric alkynylation of aldehyde. This was followed by readily handled selective hydrogenation and lactonization in three steps with a high overall yield (86%).

AB - The protecting group free synthesis of Anomala Osakana Pheromone isomer has been achieved with high enantioselectivity (92% ee). A chiral γ-hydroxy-α, β-acetylenic ester was used as the key intermediate, which was obtained via asymmetric alkynylation of aldehyde. This was followed by readily handled selective hydrogenation and lactonization in three steps with a high overall yield (86%).

KW - asymmetric alkynylation

KW - chiral γ-butyrolactone

KW - swern oxidation

KW - total synthesis

KW - β-acetylenic ester

KW - γ-hydroxy-α

UR - https://www.scopus.com/pages/publications/77956543317

U2 - 10.1007/s11434-010-3155-y

DO - 10.1007/s11434-010-3155-y

M3 - Letter

AN - SCOPUS:77956543317

SN - 1001-6538

VL - 55

SP - 2811

EP - 2813

JO - Chinese Science Bulletin

JF - Chinese Science Bulletin

IS - 25

ER -

Asymmetric synthesis of Anomala Osakana Pheromone isomer using protecting group free strategy

Abstract

Keywords

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