Syntheses of arnottin i and arnottin II

Matthew J. Moschitto; David R. Anthony; Chad A. Lewis

doi:10.1021/acs.joc.5b00107

Syntheses of arnottin i and arnottin II

Matthew J. Moschitto, David R. Anthony, Chad A. Lewis

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31 Scopus citations

Abstract

Short total syntheses of arnottin I and II were accomplished in 5 and 6 steps, respectively. A sesamol-benzyne cycloaddition with a 3-furyl-benzoate followed by regiospecific lactonization provided rapid, large-scale access to the core of arnottin I. Saponification of arnottin I and hypervalent iodide mediated spirocyclization provided an efficient and direct preparation of racemic arnottin II.

Original language	English (US)
Pages (from-to)	3339-3342
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	80
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.5b00107
State	Published - Mar 20 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.5b00107

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abstract = "Short total syntheses of arnottin I and II were accomplished in 5 and 6 steps, respectively. A sesamol-benzyne cycloaddition with a 3-furyl-benzoate followed by regiospecific lactonization provided rapid, large-scale access to the core of arnottin I. Saponification of arnottin I and hypervalent iodide mediated spirocyclization provided an efficient and direct preparation of racemic arnottin II.",

author = "Moschitto, {Matthew J.} and Anthony, {David R.} and Lewis, {Chad A.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.joc.5b00107",

language = "English (US)",

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AU - Moschitto, Matthew J.

AU - Anthony, David R.

AU - Lewis, Chad A.

PY - 2015/3/20

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N2 - Short total syntheses of arnottin I and II were accomplished in 5 and 6 steps, respectively. A sesamol-benzyne cycloaddition with a 3-furyl-benzoate followed by regiospecific lactonization provided rapid, large-scale access to the core of arnottin I. Saponification of arnottin I and hypervalent iodide mediated spirocyclization provided an efficient and direct preparation of racemic arnottin II.

AB - Short total syntheses of arnottin I and II were accomplished in 5 and 6 steps, respectively. A sesamol-benzyne cycloaddition with a 3-furyl-benzoate followed by regiospecific lactonization provided rapid, large-scale access to the core of arnottin I. Saponification of arnottin I and hypervalent iodide mediated spirocyclization provided an efficient and direct preparation of racemic arnottin II.

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Syntheses of arnottin i and arnottin II

Abstract

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