Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran

Kozo Shishido; Koji Umimoto; Takeshi Takata; Osamu Irie; Masayuki Shibuya

doi:10.3987/com-92-6231

Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran

Heterocycles ◽

10.3987/com-92-6231 ◽

1993 ◽

Vol 36 (2) ◽

pp. 345 ◽

Cited By ~ 4

Author(s):

Kozo Shishido ◽

Koji Umimoto ◽

Takeshi Takata ◽

Osamu Irie ◽

Masayuki Shibuya

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Nitrile Oxide

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ChemInform Abstract: MODEL STUDIES FOR THE TOTAL SYNTHESIS OF THE MAYTANSINOIDS BASED ON THE INTRAMOLECULAR NITRILE OXIDE-OLEFIN (3 + 2) CYCLOADDITION REACTION

Chemischer Informationsdienst ◽

10.1002/chin.198551325 ◽

1985 ◽

Vol 16 (51) ◽

Author(s):

S. S. KO ◽

P. N. CONFALONE

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Abstract Model ◽

Model Studies

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Model studies for the total synthesis of the maytansinoids based on the intramolecular nitrile oxide-olefin [3+2] cycloaddition reaction

Tetrahedron ◽

10.1016/s0040-4020(01)96704-3 ◽

1985 ◽

Vol 41 (17) ◽

pp. 3511-3518 ◽

Cited By ~ 24

Author(s):

Soo sung Ko ◽

Pat N. Confalone

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Model Studies

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ChemInform Abstract: Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran.

ChemInform ◽

10.1002/chin.199314251 ◽

2010 ◽

Vol 24 (14) ◽

pp. no-no

Author(s):

K. SHISHIDO ◽

K. UMIMOTO ◽

T. TAKATA ◽

O. IRIE ◽

M. SHIBUYA

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Nitrile Oxide

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ChemInform Abstract: THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION (INOC) ROUTE TO THE ERGOT ALKALOIDS: USE OF THE ISOXAZOLINE TO Γ-AMINO ALCOHOL CONVERSION IN THE TOTAL SYNTHESIS OF (+)-PALICLAVINE

Chemischer Informationsdienst ◽

10.1002/chin.198440315 ◽

1984 ◽

Vol 15 (40) ◽

Author(s):

A. P. KOZIKOWSKI ◽

Y.-Y. CHEN ◽

B. C. WANG ◽

Z.-B. XU

Keyword(s):

Total Synthesis ◽

Amino Alcohol ◽

Ergot Alkaloids ◽

Nitrile Oxide ◽

Alcohol Conversion

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ChemInform Abstract: A Stereoselective Total Synthesis of 11-Oxoprogesterone, a Precursor to the Corticosteroids, via an Intramolecular Cycloaddition Reaction.

ChemInform ◽

10.1002/chin.198704324 ◽

1987 ◽

Vol 18 (4) ◽

Author(s):

H. NEMOTO ◽

M. NAGAI ◽

K. FUKUMOTO ◽

T. KAMETANI

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Intramolecular Cycloaddition

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ChemInform Abstract: Novel Trinitrogen-Containing Triheterocycles via the Intramolecular Nitrile Oxide Cycloaddition Reaction.

ChemInform ◽

10.1002/chin.201209185 ◽

2012 ◽

Vol 43 (9) ◽

pp. no-no

Author(s):

Andrew J. Ferreira ◽

Danielle M. Solano ◽

James S. Oakdale ◽

Mark J. Kurth

Keyword(s):

Cycloaddition Reaction ◽

Nitrile Oxide

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Exploring the chemo-, regio-, and stereoselectivities of the (3 + 2) cycloaddition reaction of 5,5-dimethyl-3-methylene-2-pyrrolidinone with C,N-diarylnitrones and nitrile oxide derivatives: a DFT study

Journal of Molecular Modeling ◽

10.1007/s00894-021-04911-0 ◽

2021 ◽

Vol 27 (10) ◽

Author(s):

Anthony Tawiah ◽

George Baffour Pipim ◽

Richard Tia ◽

Evans Adei

Keyword(s):

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Dft Study

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Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Tetrahedron ◽

10.1016/s0040-4020(02)00630-0 ◽

2002 ◽

Vol 58 (32) ◽

pp. 6311-6322 ◽

Cited By ~ 63

Author(s):

Paul R Sebahar ◽

Hiroyuki Osada ◽

Takeo Usui ◽

Robert M Williams

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Azomethine Ylide ◽

Dipolar Cycloaddition

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Stereoselective synthesis of azepines through the conjugate addition of formamides to nitroalkenes and subsequent intramolecular nitrile oxide cycloaddition reaction

Tetrahedron ◽

10.1016/j.tet.2008.09.070 ◽

2008 ◽

Vol 64 (49) ◽

pp. 11081-11085 ◽

Cited By ~ 9

Author(s):

Akio Kamimura ◽

Takayuki Yoshida ◽

Hidemitsu Uno

Keyword(s):

Stereoselective Synthesis ◽

Cycloaddition Reaction ◽

Conjugate Addition ◽

Nitrile Oxide

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Total synthesis of barbatane sesquiterpenes: α- and β-barbatenes, gymnomitrol, and isogymnomitrol

Canadian Journal of Chemistry ◽

10.1139/v79-545 ◽

1979 ◽

Vol 57 (24) ◽

pp. 3343-3345 ◽

Cited By ~ 10

Author(s):

Mitsuaki Kodama ◽

Toshio Kurihara ◽

Jinko Sasaki ◽

Shô Itô

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Skeletal Rearrangements

A total synthesis of the barbatenes and a formal total synthesis of gymnomitrol and isogymnomitrol were achieved through a common intermediate utilizing a cycloaddition reaction and skeletal rearrangements.

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