Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling

Taehyeong Kim; Sung Il Lee; Sejin Kim; Su Yong Shim; Do Hyun Ryu

doi:10.1016/j.tet.2019.130593

Total synthesis of PGF_2α and 6,15-diketo-PGF_1α and formal synthesis of 6-keto-PGF_1α via three-component coupling

Taehyeong Kim
, Sung Il Lee
, Sejin Kim
, Su Yong Shim
, Do Hyun Ryu

Department of Chemistry

Sungkyunkwan University
Korea Basic Science Institute

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

7 Scopus citations

Abstract

The asymmetric total synthesis of PGF_2α and 6,15-diketo-PGF_1α and formal synthesis of 6-keto-PGF_1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF_2α, 6,15-diketo-PGF_1α and 6-keto-PGF_1α.

Original language	English
Article number	130593
Journal	Tetrahedron
Volume	75
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2019.130593
State	Published - 18 Oct 2019

Keywords

6-Keto-PGF
Asymmetric synthesis
Metathesis
PGF
Three-component coupling

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10.1016/j.tet.2019.130593

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title = "Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling",

abstract = "The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.",

keywords = "6-Keto-PGF, Asymmetric synthesis, Metathesis, PGF, Three-component coupling",

author = "Taehyeong Kim and Lee, \{Sung Il\} and Sejin Kim and Shim, \{Su Yong\} and Ryu, \{Do Hyun\}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = oct,

day = "18",

doi = "10.1016/j.tet.2019.130593",

language = "English",

volume = "75",

journal = "Tetrahedron",

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TY - JOUR

T1 - Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling

AU - Kim, Taehyeong

AU - Lee, Sung Il

AU - Kim, Sejin

AU - Shim, Su Yong

AU - Ryu, Do Hyun

PY - 2019/10/18

Y1 - 2019/10/18

N2 - The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.

AB - The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.

KW - 6-Keto-PGF

KW - Asymmetric synthesis

KW - Metathesis

KW - PGF

KW - Three-component coupling

UR - https://www.scopus.com/pages/publications/85072222596

U2 - 10.1016/j.tet.2019.130593

DO - 10.1016/j.tet.2019.130593

M3 - Article

AN - SCOPUS:85072222596

SN - 0040-4020

VL - 75

JO - Tetrahedron

JF - Tetrahedron

IS - 42

M1 - 130593

ER -

Total synthesis of PGF_2α and 6,15-diketo-PGF_1α and formal synthesis of 6-keto-PGF_1α via three-component coupling

Abstract

Keywords

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