Biogenesis, Occurrence, and Biological Activity

A monograph on the chemotaxonomy of flowering plants extensively lists plant products and their occurrence by broad chemical type 68 however, lists are not complete, as of 1969, and detailed references are not usually given. A classic lexicon of fragrant materials has been completely revised,69 a review of essential oil analysis covering the period September 1972 to August 1974 has been published,70 and volatile leaf oil analysis in chemosystematic studies has been reviewed.71 

Synthesis of labelled mevalonolactones continues to receive attention,47,72 and new syntheses of ( )-, (R)-, and (S)-mevalonolactones have been reported.73 The isolation74 of the energy-rich carboxylic ester (23) of prenyl mercaptan prompts the 

Guenther, G. Gilbertson, and R. T. Koenig, Analyt. Chem., 1975, 47, 139R. 

Hirata, T. Shishibori, and K. Tange, Chem. Letters, 1974, 189. 

A Pseudomonas strain hydroxylates p-menthane to cis-p-menthan-l-ol,84 and microbiological reduction of carvotanacetone with Pseudomonas ovalis gives similar results85 to those obtained with carvone (Vol. 5, p. 24, incorrectly reports inversion at C-4). (—)-Carvotanacetone (30) gives (+)-carvomenthone (31), (—)- 

Microbial transformations of monoterpenoids have been reviewed with a literature coverage to 1973/74.  

Tanaka, N. Yamagishi, R. Tanikaga, and A. Kaji, Chem. Letters, 1977, 471. 

Taguchi, H. Yamamoto, and H. Nozaki, Bull. Chem. Soc. Japan, 1977, SO, 1592. 

84 in Vol. 7, p. 8 should read D. L. J. Opdyke, Food and Cosmetics Toxicol., 1975, 13 suppl., 681 (Special Issue II Monographs on Fragrance Raw Materials) for the first special issue in this series, see D. L. J. Opdyke, ibid., 1974, 12 suppl., 807. 

A monograph on fragrance raw materials has been published as well as two useful, if dated, collections of papers on essential oils.  

Corey and M. G. Bock, Tetrahedron Letters, 1975, 3269 K. Yamada, K. Kato, H. Nagase, and Y. Hirata, Tetrahedron Letters, 1976, 65. 

Opdyke, Food and Cosmetics Technology, Vol. 13 Supplement Monographs on Fragrance Raw Materials , Pergamon, 1975. 

There has been considerable progress in the study of monoterpenoid biosynthesis. This is reviewed in Chapter 6. 

Fungal metabolism of methyl geranate by Colletotrichum nicotianae affords methyl / -(+ 6,7-dihydroxygeranate in 85% yield via methyl 5-(—)-6,7-epoxygeranate. Pseudomonas aeruginosa converts a-terpineol into p-mentha-1,4(8)-diene and borneol.  

---

In the present review, we summarize the occurrence, biogenesis, biological activity, and the chemistry of carbazole alkaloids, which have been classified based on their natural sources, ring system, and substitution pattern. While a comprehensive overview is given on all carbazole alkaloids isolated from natural sources, only their total syntheses published since 1990 are discussed. 

Multicomponent reactions in alkaloid-based drug discovery 12KGS38. Muscarine, imidazole, oxazole, and thiazole alkaloids 13NPR869. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids 12CRV3193. 

---