Chemistry of the Podocarpaceae. XXVI. Ring-c modification of 12-Hydroxypodocarpa-8,11,13-trien-19-oic acid

Cambie, R. C.; Denny, W. A.; Klose, T. R.; Mander, LN

doi:10.1071/ch9710099

Cited by 8 publications

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“…When the first reduction step is followed by alkylation at C-1, further reduction by the above routes is clearly proscribed. The diene acid can still be isomerized by strong bases, however, and the resulting conjugated diene can be reduced, as illustrated by the sequence that is outlined in Scheme 34, leading to the analogue (204) of the plant growth regulator helminthosporic acid (205).…”

Section: Tetrahydrobenzoic Acidsmentioning

confidence: 99%

Recent developments in the Birch reduction of aromatic compounds: applications to the synthesis of natural products

Hook¹,

Mander²

1986

Nat. Prod. Rep.

108

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Reviewing the literature published to May 1985 L 2.1 2.2 I-Naphthoic Acids 7.6 Di hydrophenan threnones 8.1 Arylsilanes 8.2 Benzylsilanes 9.1 Hydrogenolysis of Nuclear Substituents 8 Reduction of Aryl-and Benzyl-silanes 9 Reductive Fission of Hetero-substituents 9.1.1 Simple Ethers 9.1.2 Deoxygenation of Phenols 9.1.3 Alkoxy-substituted Aromatic Acids and Ketones 9.2.1 Benzylic Alcohols 9.2.2 Benzylic Acetals 9.2.3 Benzylic Amines 9.2 Hydrogenolysis of Benzylic Substituents 10 Conclusion 1 1 References * This review was prepared to mark the occasion of the 70th birthday of Professor 2-Acetylnaphthalenes Birch on 3rd August 1985.

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Section: Tetrahydrobenzoic Acidsmentioning

confidence: 99%

Recent developments in the Birch reduction of aromatic compounds: applications to the synthesis of natural products

Hook¹,

Mander²

1986

Nat. Prod. Rep.

108

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“…This assignment is supported by the appearance of fragments a-d in the hrms. Nimbosone {5} is the first naturally occurring aromatic tricyclic diterpenoid with an acetyl group on any one of the aromatic carbons, although such methyl ketones have been prepared from podocarpanoids (22).…”

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confidence: 99%

Tricyclic Diterpenoids from the Stem Bark of Azadirachta indica

Ara¹,

Siddiqui²,

Faizi³

et al. 1988

J. Nat. Prod.

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Nimosone, nimbosone, methyl nimbiol, and methyl nimbionone, four new tricyclic diterpenoids, have been isolated from the stem bark of Azadirachta indica along with sugiol. The structures of the new constituents have been elucidated as 12-hydroxy-8,11,13abietatriene-3,7-dione [1], 13-acetyl-12-methoxy-8,11,13-podocarpatriene {5], 12-methoxy-13-methyl-8,ll,13-podocarpatrien-7-one [6], and 12,13-dimethoxy-8,11,13-podocarpatriene-3,7-dione [7], respectively, through chemical and spectral studies. Compounds 6 and 7 have previously been reported only as reaction products.Azadirachta indica A. Juss. (Meliaceae), commonly known as "neem," is indigenous to the Indo-Pakistan subcontinent. Almost every part of the tree has been used for the treatment

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TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

134

138

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The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

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Chemistry of the Podocarpaceae. XXVI. Ring-c modification of 12-Hydroxypodocarpa-8,11,13-trien-19-oic acid

Cited by 8 publications

References 0 publications

Recent developments in the Birch reduction of aromatic compounds: applications to the synthesis of natural products

Recent developments in the Birch reduction of aromatic compounds: applications to the synthesis of natural products

Tricyclic Diterpenoids from the Stem Bark of Azadirachta indica

TheBirch Reduction of Aromatic Compounds

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