ChemInform Abstract: SYNTHESIS OF THE SPIROSESQUITERPENE (-)-ACORENONE AND RELATED CYCLOPENTANOID MONOTERPENES

G. L. LANGE; E. E. NEIDERT; W. J. ORROM; D. J. WALLACE

doi:10.1002/chin.197840309

ChemInform Abstract: SYNTHESIS OF THE SPIROSESQUITERPENE (-)-ACORENONE AND RELATED CYCLOPENTANOID MONOTERPENES

Chemischer Informationsdienst ◽

10.1002/chin.197840309 ◽

1978 ◽

Vol 9 (40) ◽

Author(s):

G. L. LANGE ◽

E. E. NEIDERT ◽

W. J. ORROM ◽

D. J. WALLACE

Keyword(s):

Cyclopentanoid Monoterpenes

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ChemInform Abstract: A GENERAL, ENANTIOSPECIFIC SYNTHESIS OF CYCLOPENTANOID MONOTERPENES (IRIDOIDS). THE TOTAL SYNTHESIS OF (-)-1-O-METHYLSWEROSIDE AGLYCON

Chemischer Informationsdienst ◽

10.1002/chin.198452327 ◽

1984 ◽

Vol 15 (52) ◽

Author(s):

T. IKEDA ◽

C. R. HUTCHINSON

Keyword(s):

Total Synthesis ◽

Cyclopentanoid Monoterpenes ◽

Enantiospecific Synthesis

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Three New Cyclopentanoid Monoterpenes fromPicrorhiza scrophulariiflora

Planta Medica ◽

10.1055/s-2004-818957 ◽

2004 ◽

Vol 70 (4) ◽

pp. 382-384 ◽

Cited By ~ 6

Keyword(s):

Cyclopentanoid Monoterpenes

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Efficient Oxidative Radical Cyclizations of Ester Enolates with Carbocation Desilylation as Termination: Synthesis of Cyclopentanoid Monoterpenes and Analogues†

Organic Letters ◽

10.1021/ol036233n ◽

2004 ◽

Vol 6 (2) ◽

pp. 257-260 ◽

Cited By ~ 30

Author(s):

Ullrich Jahn ◽

Philip Hartmann ◽

Emmi Kaasalainen

Keyword(s):

Radical Cyclizations ◽

Cyclopentanoid Monoterpenes

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Transannular cyclizations. Stereoselective synthesis of the cyclopentanoid monoterpenes

The Journal of Organic Chemistry ◽

10.1021/jo00910a045 ◽

1975 ◽

Vol 40 (22) ◽

pp. 3312-3313 ◽

Cited By ~ 27

Author(s):

Randall S. Matthews ◽

James K. Whitesell

Keyword(s):

Stereoselective Synthesis ◽

Cyclopentanoid Monoterpenes

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Two new antibiotic cyclopentanoid monoterpenes of plant origin

Tetrahedron ◽

10.1016/s0040-4020(01)99179-3 ◽

1964 ◽

Vol 20 (7) ◽

pp. 1781-1787 ◽

Cited By ~ 27

Author(s):

W.H. Tallent

Keyword(s):

Plant Origin ◽

Cyclopentanoid Monoterpenes

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Monoterpenes of Teucrium marum

Australian Journal of Chemistry ◽

10.1071/ch9761375 ◽

1976 ◽

Vol 29 (6) ◽

pp. 1375 ◽

Cited By ~ 63

Author(s):

UM Pagnoni ◽

A Pinetti ◽

R Trave ◽

L Garanti

Keyword(s):

Chemical Transformations ◽

Cyclopentanoid Monoterpenes ◽

Unsaturated Lactones

Four cyclopentanoid monoterpenes were isolated from Teucrium marum; they are the two [(A) and (B)] C2-epimers of a-(2-formyl-3-methylcyclopentyl)acrylaldehyde and two new [(C) and (D)] isomeric unsaturated lactones. Structures were established by spectral (u.v., i.r., N.M.R., m.s.) evidence and chemical transformations.

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Synthesis of the spirosesquiterpene (−)-acorenone and related cyclopentanoid monoterpenes

Canadian Journal of Chemistry ◽

10.1139/v78-266 ◽

1978 ◽

Vol 56 (12) ◽

pp. 1628-1633 ◽

Cited By ~ 33

Author(s):

Gordon L. Lange ◽

Eli E. Neidert ◽

Will J. Orrom ◽

David J. Wallace

Keyword(s):

Acetic Acid ◽

Total Synthesis ◽

Absolute Configuration ◽

Optically Active ◽

Starting Material ◽

Critical Step ◽

Naturally Occurring ◽

Toluenesulfonic Acid ◽

Methylmagnesium Iodide ◽

Cyclopentanoid Monoterpenes

The first total synthesis of the spirosesquiterpene (−)-acorenone (1) is described. The critical step involves a spiroannelation of the enamine of aldehyde 11 with 1-methoxy-3-buten-2-one (16) in the presence of acetic acid to give ketone 17. Reaction of 17 with methylmagnesium iodide followed by treatment of the resultant alcohol 18 with p-toluenesulfonic acid in refluxing benzene leads directly to 1 in good overall yield. As the starting material for the preparation of the cyclopentanoid aldehyde 11 was (+)-limonene the final product is optically active and thus the absolute configuration of naturally occurring (−)-acorenone (1) is established. The preparation of a number of other optically active cyclopentanoid monoterpenes (4 and 13) is also described.

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