In the twelve years since the first review article dealing with chemical constituents of the Hepaticae appeared in this series as Volume 42 (19), several short reviews concerned with chemical constituents of bryophytes have been published (22, 96, 144, 265, 271, 647, 649, 650) In 1988, a Symposium on Chemistry and Chemical Taxonomy of Bryophytes was organised on the behalf of the Phytochemical Society of Europe; the proceedings of this meeting appeared as a book entitled Bryophytes: Their Chemistry and Chemical Taxonomy (651) The symposium concerned itself with phytochemical, biochemical, botanical, chemotaxonomical, pharmaceutical, biotechnological and environmental aspects of bryophytes as well as with the synthesis of the terpenoids and aromatic compounds bryophytes elaborate The physiological and biochemical aspects of bryophytes have also been described in a recent book Bryophytes Development: Physiology and Biochemistry (139)

Chemical Constituents of the Bryophytes

The synthesis of carbocyclic eight-membered rings

Chemosystematics of the hepaticae.

Cyclopentane-forming di/sesterterpene synthases: widely distributed enzymes in bacteria, fungi, and plants.

A synthetic pathway leading to (+)-fusicoauritone (1) is highlighted by the use of a Julia condensation for preparation of an eleven-membered dolabelladienone precursor for subsequent Nazarov cyclization to yield the 5-8-5 tricyclic diterpene skeleton.

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Strategies for the Synthesis of Fusicoccanes by Nazarov Reactions of Dolabelladienones: Total Synthesis of (+)-Fusicoauritone

Anadensin, a new fusicoccane diterpenoid from the liverwort . Crystal structure analysis.

The dolabellane diterpenoids 10R,18-diacetoxy-3S,4S;7S,8S-diepoxydolabellane (barbilycopodin)(1), 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene (12), 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane (4), and 18-hydroxydolabell-7E-en-3-one (14) have been isolated from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata. The 1H and 13C n.m.r. spectroscopic properties of the compounds and some of their transformation products are described. The structures, relative stereochemistries, and conformations of compounds (4), (12), and 3S,4S,7S,8S-diepoxy-10R,18-dihydroxydolabellane (2) were defined by X-ray crystallographic studies. The eleven-membered ring has essentially the same conformation in compounds (2), (4), and (12), a conformation which has been characterised as a low-energy form of cycloundeca-1,5-diene by molecular-mechanics calculations.

Dolabellane diterpenoids from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata: spectroscopic and X-ray studies of structure, stereochemistry, and conformation. X-Ray molecular structure of 3S,4S;7S,8S-diepoxy-10R,18-dihydroxydollabellane, 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane, and 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene

George A. Baxter

Papers

Anadensin, a new fusicoccane diterpenoid from the liverwort . Crystal structure analysis.