BOOK REVIEWS 417 many of the structural studies reported rely heavily on instrumentation. In a useful historical review, S. Sugasawa, traces the development of organic chemistry in Japan up to 1940, from early training in the famous fin de siecle European schools of Willstatter, Hofmann and Emil Fischer. Investigations in agricultural chemistry include various vital growth factors derived from rice, and naturally occurring pesticides. The pharmaceutical field embraces classical work on ephedrine and its congeners, and more recent attention to the amaryllidaceae alkaloids. Reference is made to the impressive contribution made to lichen chemistry by Prof. Asahina. Other groups of plant products studied include components of Japan lacquer, phenolic pigments, heartwood tropolones, triterpenes, flayones and biflavones fish toxins and hormone and bite steroids are cited as examples of studies on factors of animal origin. Prof. Buchi (M.I.T.) concerns himself with the chemistry of certain dimeric indole alkaloids. The special interest in bisindoles derives from calabash curare, but at least three types of linkage are now distinguished simple dimers such as dihydrotoxiferin-C, an aminoacetal, e.g. geissosper- mine, and C-C linked moieties, as occur in a number of Voacanga and Vinca rosea bases intensive interest in the latter bisindoles has been prompted by their reputed anti-tumour activity. Particular emphasis is laid on the support that mass-spectroscopic and NMR studies have given to the elucidation of these exceedingly diverse series of indole alkaloids. Prof. D. H. R. Barton (Imperial College, London) traces his active interest in biogenesis from his revision of the structure of Pummerer's ketone (the crystalline oxidation product of pcresol) and an elegant syn- thesis of the lichen product usnic acid. He proceeds from a generalisation of phenolate radical coupling to a lucid exposition of mechanisms of alkaloid biogenesis, giving special attention to a derivation of the morphine group from a benzylisoquinoline tricyclic intermediate, to demonstration of the natural occurrence of dienone isoquinoline intermediates in bio- genesis of the apophine series and to speculation regarding the interrelation- ships of the Stephanie alkaloids. Prof. R. B. Woodward (Harvard) follows with a fascinating account of the elucidation of the structure of one of the most virulent poisons known: Tetrodotoxin- found in some organs of Japanese puffer fish. The in- vestigation is notable for many features, including the considerable initial difficulty of obtaining crystalline substances to determine even the mole- cular formula, the diagnostic use of NMR spectroscopy at every stage, the caution in interpreting facile rearrangements in a polyfunctional

418 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS product and the presence of a hemilactal system- entirely unique in natural and synthetic products. Shemyakin and Antonov (Moscow Natural Products Institute) present a most useful review of intramolecular enzymic transpeptidation. They cite examples of formation of N-acyl amides important in metabolism and biosynthesis and of the determination of structures resulting from incor- poration of hydroxyl or aminoacyl groups, using UV, IR, NMR and mass spectroscopy. They discuss the criticality of ring size in the expansion of N-acyl cyclic lactams to form peptide lactones and outline a number of biogenetic pathways for peptide antibiotics such considerations may also be applied to proteins and hormones. K. Biemann (M.I.T.) describes in considerable detail the utility of high resolution mass spectroscopy in the examination of natural products, particularly for the very accurate determination of molecular weights and the study of fragmentation mechanisms leading to structural assignments. There are two distinct systems: Both employ preliminary electrostatic focussing in addition to the conventional electromagnetic stage. Beynon employs a single focus low resolution scan followed by double focussing to examine peaks of special interest. Biemann considers this time- consuming for general use he employs a computer to analyse a photo- graphic record of a complete HR mass spectrum, which assigns mass with a precision of one part in 100,000 by comparison with an internal standard, and is then able to deduce the correct elemental composition of fragments that are superposed in conventional low resolution instruments. Examples from steroid and alkaloid fields, using both techniques, are discussed in detail one at present totally unknown structure is included to demonstrate the 'potential of his version. Prof. V. Prelog (ETH, Zurich) refers to his earlier examination of micro- biological reduction of alicyclic ketones (especially d ecalin-l,4-diones), frequently with the production of a preferred enantiomer, which has led naturally into an investigation of product stereospecificity in enzyme reactions. Whilst the enzyme infra-structure plays an important role, such interaction cannot be the sole factor. The development of Prelog's diamond lattice theory for the spatial relation of the reactive groups is therefore particularly significant. Prof. Stork (Columbia University, New York) gives a detailed account of annelation reactions that he has found especially useful in the total synthesis of natural alicyclic systems. Having shown his versatility in the construction of steroid rings B and A, from a basic decalenone starting