Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester

Bao Hu; Siyang Xing; Jun Ren; Zhongwen Wang

doi:10.1016/j.tet.2010.05.057

Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester

Bao Hu
, Siyang Xing
, Jun Ren
, Zhongwen Wang

Psychiatry

Nankai University

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

47 Scopus citations

Abstract

Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products.

Original language	English
Pages (from-to)	5671-5674
Number of pages	4
Journal	Tetrahedron
Volume	66
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2010.05.057
State	Published - Jul 24 2010

Keywords

Bruguierol Total synthesis Nature product Cycloaddition Cyclopropane

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10.1016/j.tet.2010.05.057

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title = "Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester",

abstract = "Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8\% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products.",

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AU - Hu, Bao

AU - Xing, Siyang

AU - Ren, Jun

AU - Wang, Zhongwen

PY - 2010/7/24

Y1 - 2010/7/24

N2 - Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products.

AB - Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products.

KW - Bruguierol Total synthesis Nature product Cycloaddition Cyclopropane

UR - https://www.scopus.com/pages/publications/77955919596

U2 - 10.1016/j.tet.2010.05.057

DO - 10.1016/j.tet.2010.05.057

M3 - Article

AN - SCOPUS:77955919596

SN - 0040-4020

VL - 66

SP - 5671

EP - 5674

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester

Abstract

Keywords

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