A ring-closing metathesis approach to the bicyclo 4.3.1 decane core of caryolanes

W. P. D. Goldring, W. T. Paden

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.
OriginalsprogEngelsk
TidsskriftTetrahedron Letters
Vol/bind52
Udgave nummer8
Sider (fra-til)859-862
Antal sider4
ISSN0040-4039
DOI
StatusUdgivet - 2011
Udgivet eksterntJa

Citer dette

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abstract = "A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.",
author = "Goldring, {W. P. D.} and Paden, {W. T.}",
year = "2011",
doi = "10.1016/j.tetlet.2010.11.138",
language = "English",
volume = "52",
pages = "859--862",
journal = "Tetrahedron Letters",
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A ring-closing metathesis approach to the bicyclo 4.3.1 decane core of caryolanes. / Goldring, W. P. D.; Paden, W. T.

I: Tetrahedron Letters, Bind 52, Nr. 8, 2011, s. 859-862.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - A ring-closing metathesis approach to the bicyclo 4.3.1 decane core of caryolanes

AU - Goldring, W. P. D.

AU - Paden, W. T.

PY - 2011

Y1 - 2011

N2 - A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.

AB - A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.

U2 - 10.1016/j.tetlet.2010.11.138

DO - 10.1016/j.tetlet.2010.11.138

M3 - Journal article

VL - 52

SP - 859

EP - 862

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -