Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products

Kok Ping Chan; Teck Peng Loh

doi:10.1021/ol051951q

Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products

Kok Ping Chan, Teck Peng Loh

Nanyang Technological University

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

119 Scopus citations

Abstract

(Chemical Equation Presented) A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.

Original language	English
Pages (from-to)	4491-4494
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	20
DOIs	https://doi.org/10.1021/ol051951q
State	Published - 29 Sep 2005
Externally published	Yes

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abstract = "(Chemical Equation Presented) A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.",

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AB - (Chemical Equation Presented) A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.

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Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products

Abstract

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