Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

Jonathan S. Foot; Andrew T. Phillis; Phillip P. Sharp; Anthony C. Willis; Martin G. Banwell

doi:10.1016/j.tetlet.2006.07.068

Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

Jonathan S. Foot
, Andrew T. Phillis
, Phillip P. Sharp
, Anthony C. Willis
, Martin G. Banwell^*

^*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown

Original language	English
Pages (from-to)	6817-6820
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.068
Publication status	Published - 18 Sept 2006

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@article{a059be9a25c9466e8e152aea8877ae2c,

title = "Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A",

abstract = "A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown",

keywords = "Cyclopropene, Dichlorocyclopropane, Furan, Furanosesquiterpene, Pallescensin A, Wieland-Miescher ketone",

author = "Foot, \{Jonathan S.\} and Phillis, \{Andrew T.\} and Sharp, \{Phillip P.\} and Willis, \{Anthony C.\} and Banwell, \{Martin G.\}",

year = "2006",

month = sep,

day = "18",

doi = "10.1016/j.tetlet.2006.07.068",

language = "English",

volume = "47",

pages = "6817--6820",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "38",

}

TY - JOUR

T1 - Dichlorocarbene adducts of alkyl enol ethers as precursors to furans

T2 - application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

AU - Foot, Jonathan S.

AU - Phillis, Andrew T.

AU - Sharp, Phillip P.

AU - Willis, Anthony C.

AU - Banwell, Martin G.

PY - 2006/9/18

Y1 - 2006/9/18

N2 - A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown

AB - A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown

KW - Cyclopropene

KW - Dichlorocyclopropane

KW - Furan

KW - Furanosesquiterpene

KW - Pallescensin A

KW - Wieland-Miescher ketone

UR - https://www.scopus.com/pages/publications/33747190017

U2 - 10.1016/j.tetlet.2006.07.068

DO - 10.1016/j.tetlet.2006.07.068

M3 - Article

SN - 0040-4039

VL - 47

SP - 6817

EP - 6820

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

Abstract

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