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By J R Hanson; Royal Society of Chemistry

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Example text

The ethylene bridge was then cleaved to create the two requisite methyl groups. Interestingly the first intramolecular Michael reaction [(285) + (286)] could be achieved with (-)quinine as the base and this produced the optically active ketone (286) with one enantiomer in excess (65%) of the other (35%). 136 137 13' H. Takeshita, H. Iwabuchi, I. Kouno, M. Iino, and D. Nomura, Chem. , 1979, 649. C. Misra and A. Ghosh, Synth. , 1 9 7 8 , 8 , 4 0 3 . B. M. Trost, C. D. Shuey, and F. , J. Am. Chem.

Ed. , 1979, 18, 163. 'l have appended the two requisite side-chains (119) which can be lactonized with di-(2-pyridyl) disulphide and triphenylphosphine to give tetrahydroverrucarin J (120). A recent investigation of the biosynthesis of trichodermin (121) using [l-13C]acetate is in accord with an earlier result although some reassignments of certain chemical shifts have been ~ u g g e s t e d . 73 The halogenated chamigranes and related metabolites from the marine algae of the genus Laurencia continue to be actively investigated, with X-ray analysis 69 70 71 72 73 E.

99. 95 K. Rajendran, S. K. Paknikar, G. K. Trivedi, andS. C. Bhattacharyya, IndianJ. ,Sect. B, 1978, 16,4. r. "' A (172) (173) R (174) R = = H OH M. Rohr and P. Naegeli, Phytochemistry, 1979,18, 328. F. Bohlmann, C. Zdero, R. M. King, and H. Robinson, Phytochemistry, 1979,18, 1177. 98 F. Bohlmann and C. Zdero, Phytochemistry, 1979,18, 1185. 99 P. S. Kalsi, G. S. Arora, and R. S. Ghulati, Phytochemistry, 1979,18, 1223; R. C. Agrawal, T. D. Audichya, G. K. Trivedi, and S. C. Bhattacharyya, Indian J.

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