Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

Journal of the American Chemical Society ◽

10.1021/ja00542a060 ◽

1980 ◽

Vol 102 (22) ◽

pp. 6893-6894 ◽

Author(s):

William G. Dauben ◽

Carl R. Kessel ◽

Kazuo H. Takemura

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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Chiral Synthesis of Erythrina Alkaloids. I Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.41.2087 ◽

1993 ◽

Vol 41 (12) ◽

pp. 2087-2095 ◽

Author(s):

Yoshisuke TSUDA ◽

Shinzo HOSOI ◽

Nobuya KATAGIRI ◽

Chikara KANEKO ◽

Takehiro SANO

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Chiral Synthesis ◽

Diels Alder Reaction ◽

Erythrina Alkaloids

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Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction Under Super High Pressure

Heterocycles ◽

10.3987/com-91-s65 ◽

1992 ◽

Vol 33 (2) ◽

pp. 497 ◽

Author(s):

Yoshisuke Tsuda ◽

Shinzo Hosoi ◽

Nobuya Katagiri ◽

Chikara Kaneko ◽

Takehiro Sano

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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ChemInform Abstract: SIMPLE, EFFICIENT TOTAL SYNTHESIS OF CANTHARIDIN VIA A HIGH-PRESSURE DIELS-ALDER REACTION

Chemischer Informationsdienst ◽

10.1002/chin.198104349 ◽

1981 ◽

Vol 12 (4) ◽

Author(s):

W. G. DAUBEN ◽

C. R. KESSEL ◽

K. H. TAKEMURA

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

The Journal of Organic Chemistry ◽

10.1021/jo970444m ◽

1997 ◽

Vol 62 (16) ◽

pp. 5299-5309 ◽

Author(s):

Yoshitaka Araki ◽

Toshiro Konoike

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Enantioselective Total Synthesis ◽

Diels Alder Reaction ◽

Efficient Construction

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ChemInform Abstract: Synthesis of Erythrina and Related Alkaloids. Part 40. Chiral Synthesis of Erythrina Alkaloids. Part 1. Total Synthesis of (+)- Erysotrine via Asymmetric Diels-Alder Reaction Under High Pressure.

10.1002/chin.199425216 ◽

2010 ◽

Vol 25 (25) ◽

pp. no-no

Author(s):

Y. TSUDA ◽

S. HOSOI ◽

N. KATAGIRI ◽

C. KANEKO ◽

T. SANO

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Chiral Synthesis ◽

Diels Alder Reaction ◽

Erythrina Alkaloids

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Towards the total synthesis of colletofragarones: constructing the macrocyclic lactone by high pressure-mediated intramolecular Diels–Alder reaction

Tetrahedron Letters ◽

10.1016/j.tetlet.2009.03.063 ◽

2009 ◽

Vol 50 (26) ◽

pp. 3574-3576 ◽

Author(s):

Joaquín G. Marrero ◽

Laurence M. Harwood

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Macrocyclic Lactone ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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ChemInform Abstract: Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogues. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels-Alder Reaction of (R,2Z, 8E,10E)-1-((tert-Butyldimethy

10.1002/chin.199752253 ◽

2010 ◽

Vol 28 (52) ◽

pp. no-no

Author(s):

Y. ARAKI ◽

T. KONOIKE

Keyword(s):

High Pressure ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Enantioselective Total Synthesis ◽

Diels Alder Reaction ◽

Efficient Construction

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ChemInform Abstract: Synthesis of Naturally Occurring Quinones. Part 18. Trichloro-(trans2,4-pentadienyl)stannane as a Less Electron-Rich Diene and Its Application to Tandem Michael/Diels-Alder Reaction. Formal Total Synthesis of 11-Deoxydaunomycinone.

10.1002/chin.198717176 ◽

1987 ◽

Vol 18 (17) ◽

Author(s):

Y. NARUTA ◽

Y. NISHIGAICHI ◽

K. MARUYAMA

Keyword(s):

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Naturally Occurring

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Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 2 [1]: Macrocyclization and Diels-Alder reaction

Tetrahedron Letters ◽

10.1016/s0040-4039(99)00324-x ◽

1999 ◽

Vol 40 (14) ◽

pp. 2769-2772 ◽

Author(s):

András Toró ◽

Yuan Wang ◽

Marc Drouin ◽

Pierre Deslongchamps

Keyword(s):

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Model Studies ◽

Diels Alder Reaction

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Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.63 ◽

2015 ◽

Vol 11 ◽

pp. 576-582 ◽

Author(s):

Grzegorz Mlostoń ◽

Paulina Grzelak ◽

Maciej Mikina ◽

Anthony Linden ◽

Heinz Heimgartner

Keyword(s):

High Pressure ◽

Room Temperature ◽

Thermal Conditions ◽

Alder Reaction ◽

Diels Alder ◽

Hydrogen Shift ◽

Diels Alder Reaction ◽

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

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