Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates

Stacie A. Calad; Jelena Ćiraković; K. A. Woerpel

doi:10.1021/jo0620011

Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates

Stacie A. Calad, Jelena Ćiraković, K. A. Woerpel

Chemistry

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

Abstract

(Chemical Equation Presented) The synthesis of (±)-1′-epi- stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.

Original language	English (US)
Pages (from-to)	1027-1030
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	3
DOIs	https://doi.org/10.1021/jo0620011
State	Published - Feb 2 2007

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo0620011

Cite this

@article{a4e1bf50c14b44eea8cbb1965ad1919e,

title = "Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates",

abstract = "(Chemical Equation Presented) The synthesis of (±)-1′-epi- stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.",

author = "Calad, {Stacie A.} and Jelena {\'C}irakovi{\'c} and Woerpel, {K. A.}",

year = "2007",

month = feb,

day = "2",

doi = "10.1021/jo0620011",

language = "English (US)",

volume = "72",

pages = "1027--1030",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates

AU - Calad, Stacie A.

AU - Ćiraković, Jelena

AU - Woerpel, K. A.

PY - 2007/2/2

Y1 - 2007/2/2

N2 - (Chemical Equation Presented) The synthesis of (±)-1′-epi- stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.

AB - (Chemical Equation Presented) The synthesis of (±)-1′-epi- stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.

UR - http://www.scopus.com/inward/record.url?scp=33846896658&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33846896658&partnerID=8YFLogxK

U2 - 10.1021/jo0620011

DO - 10.1021/jo0620011

M3 - Article

C2 - 17253829

AN - SCOPUS:33846896658

SN - 0022-3263

VL - 72

SP - 1027

EP - 1030

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this