Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones
Publication type: Journal Article
Publication date: 2017-09-04
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The preparation of (E)-4-methylhexa-3,5-dien-1-ol has been achieved in a single step from 3-methylpenta-1,4-diene through deprotonation with BuLi, alkylation with paraformaldehyde and metal-counterion exchange in situ to promote oxy-anion-accelerated [1,3]-sigmatropic shift. This alcohol is shown to undergo intermolecular Diels–Alder reaction with 3-isopropyl acrylate thioesters; the so-formed exclusive endo-adduct may then be closed to the bicyclic lactone, the product of formal intramolecular Diels–Alder reaction (a much more difficult process). Use of chiral thioesters results in an enantioselective synthesis of this bicyclic lactone, an intermediate with application to eunicellane (cladiellane) diterpene synthesis.
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Total citations:
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Citations from 2024:
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Syntrivanis L. D., Robertson J. Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 33. pp. 4916-4921.
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Syntrivanis L. D., Robertson J. Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 33. pp. 4916-4921.
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TY - JOUR
DO - 10.1002/ejoc.201700900
UR - https://doi.org/10.1002/ejoc.201700900
TI - Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones
T2 - European Journal of Organic Chemistry
AU - Syntrivanis, Leonidas Dimitrios
AU - Robertson, Jeremy
PY - 2017
DA - 2017/09/04
PB - Wiley
SP - 4916-4921
IS - 33
VL - 2017
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2017_Syntrivanis,
author = {Leonidas Dimitrios Syntrivanis and Jeremy Robertson},
title = {Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones},
journal = {European Journal of Organic Chemistry},
year = {2017},
volume = {2017},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/ejoc.201700900},
number = {33},
pages = {4916--4921},
doi = {10.1002/ejoc.201700900}
}
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Syntrivanis, Leonidas Dimitrios, and Jeremy Robertson. “Synthesis of (E )-4-Methylhexa-3,5-dien-1-ol and Its Diels-Alder Reaction with Thioester Dienophiles: A Short Enantioselective Synthesis of Bicyclic Lactones.” European Journal of Organic Chemistry, vol. 2017, no. 33, Sep. 2017, pp. 4916-4921. https://doi.org/10.1002/ejoc.201700900.