Asymmetric synthesis of (-)-pterosin N from a chiral 1,3-dioxolanone

Hsiu Han Wu; Shao Chien Hsu; Feng Lin Hsu; Biing Jiun Uang

doi:10.1002/ejoc.201402234

Asymmetric synthesis of (-)-pterosin N from a chiral 1,3-dioxolanone

Hsiu Han Wu
, Shao Chien Hsu
, Feng Lin Hsu
, Biing Jiun Uang

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研究成果: 雜誌貢獻 › 文章 › 同行評審

10 引文斯高帕斯（Scopus）

摘要

The first asymmetric total synthesis of (-)-pterosin N from the N,N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8% overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene-ynone by Stille coupling, and an intramolecular Diels-Alder reaction followed by aromatization to finish the synthesis. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

原文	英語
頁（從 - 到）	4351-4355
頁數	5
期刊	European Journal of Organic Chemistry
卷	2014
發行號	20
DOIs	https://doi.org/10.1002/ejoc.201402234
出版狀態	已發佈 - 7月 2014

ASJC Scopus subject areas

物理與理論化學
有機化學

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10.1002/ejoc.201402234

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title = "Asymmetric synthesis of (-)-pterosin N from a chiral 1,3-dioxolanone",

abstract = "The first asymmetric total synthesis of (-)-pterosin N from the N,N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8\% overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene-ynone by Stille coupling, and an intramolecular Diels-Alder reaction followed by aromatization to finish the synthesis.",

keywords = "Asymmetric synthesis, Diels-Alder reactions, Natural products, Synthetic methods, Total synthesis",

author = "Wu, \{Hsiu Han\} and Hsu, \{Shao Chien\} and Hsu, \{Feng Lin\} and Uang, \{Biing Jiun\}",

year = "2014",

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doi = "10.1002/ejoc.201402234",

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pages = "4351--4355",

journal = "European Journal of Organic Chemistry",

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T1 - Asymmetric synthesis of (-)-pterosin N from a chiral 1,3-dioxolanone

AU - Wu, Hsiu Han

AU - Hsu, Shao Chien

AU - Hsu, Feng Lin

AU - Uang, Biing Jiun

PY - 2014/7

Y1 - 2014/7

N2 - The first asymmetric total synthesis of (-)-pterosin N from the N,N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8% overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene-ynone by Stille coupling, and an intramolecular Diels-Alder reaction followed by aromatization to finish the synthesis.

AB - The first asymmetric total synthesis of (-)-pterosin N from the N,N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8% overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene-ynone by Stille coupling, and an intramolecular Diels-Alder reaction followed by aromatization to finish the synthesis.

KW - Asymmetric synthesis

KW - Diels-Alder reactions

KW - Natural products

KW - Synthetic methods

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/84903770764

UR - https://www.scopus.com/pages/publications/84903770764#tab=citedBy

U2 - 10.1002/ejoc.201402234

DO - 10.1002/ejoc.201402234

M3 - Article

AN - SCOPUS:84903770764

SN - 1434-193X

VL - 2014

SP - 4351

EP - 4355

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20

ER -

Asymmetric synthesis of (-)-pterosin N from a chiral 1,3-dioxolanone

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