Suppression of epimerization due to selectivity leakage: An application towards the total synthesis of (-)-centrolobine

Cheng Hsia Angeline Lee; Teck Peng Loh

doi:10.1016/j.tetlet.2005.12.108

Suppression of epimerization due to selectivity leakage: An application towards the total synthesis of (-)-centrolobine

Cheng Hsia Angeline Lee, Teck Peng Loh^*

^*Corresponding author for this work

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

65 Citations (Scopus)

Abstract

An InCl₃-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value of this protocol is demonstrated by the total synthesis of (-)-centrolobine.

Original language	English
Pages (from-to)	1641-1644
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2005.12.108
Publication status	Published - Mar 6 2006
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Centrolobine
Epimerization
Prins cyclization
Tetrahydropyrans

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10.1016/j.tetlet.2005.12.108

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abstract = "An InCl3-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value of this protocol is demonstrated by the total synthesis of (-)-centrolobine.",

keywords = "Centrolobine, Epimerization, Prins cyclization, Tetrahydropyrans",

author = "Lee, \{Cheng Hsia Angeline\} and Loh, \{Teck Peng\}",

year = "2006",

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T2 - An application towards the total synthesis of (-)-centrolobine

AU - Lee, Cheng Hsia Angeline

AU - Loh, Teck Peng

PY - 2006/3/6

Y1 - 2006/3/6

N2 - An InCl3-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value of this protocol is demonstrated by the total synthesis of (-)-centrolobine.

AB - An InCl3-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value of this protocol is demonstrated by the total synthesis of (-)-centrolobine.

KW - Centrolobine

KW - Epimerization

KW - Prins cyclization

KW - Tetrahydropyrans

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M3 - Article

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SN - 0040-4039

VL - 47

SP - 1641

EP - 1644

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Suppression of epimerization due to selectivity leakage: An application towards the total synthesis of (-)-centrolobine

Abstract

ASJC Scopus Subject Areas

Keywords

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