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

School of Pharmacy

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

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4351-4355
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	20
DOIs	https://doi.org/10.1002/ejoc.201402234
Publication status	Published - Jul 2014

Keywords

Asymmetric synthesis
Diels-Alder reactions
Natural products
Synthetic methods
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201402234

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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}",

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AU - Wu, Hsiu Han

AU - Hsu, Shao Chien

AU - Hsu, Feng Lin

AU - Uang, Biing Jiun

PY - 2014/7

Y1 - 2014/7

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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

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

Abstract

Keywords

ASJC Scopus subject areas

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