Biomimetic synthesis of fused bispyran: Lewis acid effects on oxacyclizations of polyepoxides

Rongbiao Tong; Frank E. McDonald; Xikui Fang; Kenneth I. Hardcastle

doi:10.1055/s-2007-983772

Biomimetic synthesis of fused bispyran: Lewis acid effects on oxacyclizations of polyepoxides

Rongbiao Tong
, Frank E. McDonald^*
, Xikui Fang
, Kenneth I. Hardcastle

^*Corresponding author for this work

Emory University

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

9 Scopus citations

Abstract

The biomimetic synthesis of fused bispyran via Lewis acid mediated tandem oxacyclization of a 1,4,7-polyepoxide is explored. The nature of the Lewis acid promoter is critical for the endo-regioselectivity of epoxide cyclization, although anomalous apparent retention of stereochemistry is observed at some reactive centers.

Original language	English
Pages (from-to)	2337-2342
Number of pages	6
Journal	Synthesis (Germany)
Issue number	15
DOIs	https://doi.org/10.1055/s-2007-983772
State	Published - 2 Aug 2007
Externally published	Yes

Keywords

Biomimetic synthesis
Fused polycyclic ethers
Polyepoxides
Regioselectivity
Stereoselectivity

Access to Document

10.1055/s-2007-983772

Cite this

@article{32afbe6992ea486d90683f171cddabe2,

title = "Biomimetic synthesis of fused bispyran: Lewis acid effects on oxacyclizations of polyepoxides",

abstract = "The biomimetic synthesis of fused bispyran via Lewis acid mediated tandem oxacyclization of a 1,4,7-polyepoxide is explored. The nature of the Lewis acid promoter is critical for the endo-regioselectivity of epoxide cyclization, although anomalous apparent retention of stereochemistry is observed at some reactive centers.",

keywords = "Biomimetic synthesis, Fused polycyclic ethers, Polyepoxides, Regioselectivity, Stereoselectivity",

author = "Rongbiao Tong and McDonald, \{Frank E.\} and Xikui Fang and Hardcastle, \{Kenneth I.\}",

year = "2007",

month = aug,

day = "2",

doi = "10.1055/s-2007-983772",

language = "英语",

pages = "2337--2342",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "15",

}

TY - JOUR

T1 - Biomimetic synthesis of fused bispyran

T2 - Lewis acid effects on oxacyclizations of polyepoxides

AU - Tong, Rongbiao

AU - McDonald, Frank E.

AU - Fang, Xikui

AU - Hardcastle, Kenneth I.

PY - 2007/8/2

Y1 - 2007/8/2

N2 - The biomimetic synthesis of fused bispyran via Lewis acid mediated tandem oxacyclization of a 1,4,7-polyepoxide is explored. The nature of the Lewis acid promoter is critical for the endo-regioselectivity of epoxide cyclization, although anomalous apparent retention of stereochemistry is observed at some reactive centers.

AB - The biomimetic synthesis of fused bispyran via Lewis acid mediated tandem oxacyclization of a 1,4,7-polyepoxide is explored. The nature of the Lewis acid promoter is critical for the endo-regioselectivity of epoxide cyclization, although anomalous apparent retention of stereochemistry is observed at some reactive centers.

KW - Biomimetic synthesis

KW - Fused polycyclic ethers

KW - Polyepoxides

KW - Regioselectivity

KW - Stereoselectivity

UR - https://www.scopus.com/pages/publications/34547735472

U2 - 10.1055/s-2007-983772

DO - 10.1055/s-2007-983772

M3 - 文章

AN - SCOPUS:34547735472

SN - 0039-7881

SP - 2337

EP - 2342

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 15

ER -

Biomimetic synthesis of fused bispyran: Lewis acid effects on oxacyclizations of polyepoxides

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this