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^*

^*Corresponding author for this work

Nanyang Technological University

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

119 Citations (Scopus)

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
Publication status	Published - Sept 29 2005
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol051951q

Cite this

@article{53ff7e5c3ed44f50ab014cced63c9c2a,

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

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.",

author = "Chan, \{Kok Ping\} and Loh, \{Teck Peng\}",

year = "2005",

month = sep,

day = "29",

doi = "10.1021/ol051951q",

language = "English",

volume = "7",

pages = "4491--4494",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Prins cyclizations in silyl additives with suppression of epimerization

T2 - Versatile tool in the synthesis of the tetrahydropyran backbone of natural products

AU - Chan, Kok Ping

AU - Loh, Teck Peng

PY - 2005/9/29

Y1 - 2005/9/29

N2 - (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.

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.

UR - http://www.scopus.com/inward/record.url?scp=26444496462&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=26444496462&partnerID=8YFLogxK

U2 - 10.1021/ol051951q

DO - 10.1021/ol051951q

M3 - Article

C2 - 16178566

AN - SCOPUS:26444496462

SN - 1523-7060

VL - 7

SP - 4491

EP - 4494

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this