By Paul J. Scheuer
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A. KNOWN TRITERPENOIDS Friedelin So far only two triterpenoids that are known constituents of terrestrial plants have been isolated from marine sources. The first such compound, friedelin (89) was identified by Tsuda and Sakai (1960) after its isolation 89 from a blue-green alga Monostroma nitidum. Although it was first isolated from cork (Friedel, 1892) in the last century, its structure was not fully elucidated until 1955 (Corey and Ursprung, 1955a,b; Dutler et al, 1955). b. Taraxerol Another triterpenoid, taraxerol (90), which is widely known from terrestrial sources, was recently isolated from the green alga Caulerpa lamourouxii by Santos and Doty (1971).
The most likely structure, norphytane (2,6,10,14-tetramethylpentadecane), 53, was synthesized from the ubiquitous plant alcohol phytol (54) and was shown to be identical with pristane (Sörensen and Sorensen, 1949). 53 ^JL^/\^ CH 2OH 54 The second hydrocarbon, the olefin zamene, was first partially characterized by Tsujimoto (1935) and shown to be 2,6,10,14-tetramethyl-l-pentadecene (55) by degradation to formaldehyde and the known 6,10,14-trimethyl2-pentadecanone (56) (Christensen and Sorensen, 1951).
1966, 1970) Irie et al. (1966, 1970) Irie et al. (1969a) Suzuki et al. (1970) Sims et al. (1971) Fenical et al. (1971); Sims et al. (1972) Text no. 6 — — Reference 18 / . Isoprenoids HO o^uY Cl Br 48 The same research group (Fenical et al, 1971) reported the isolation of a related compound, johnstonol (48), from L. johnstonii collected in the Gulf of California. The structure of johnstonol was established by single-crystal X-ray techniques (Sims et al, 1972). 1 on page 17 contains a list of characterized marine sesquiterpenoids.