By J R Hanson; R B Boar; Royal Society of Chemistry.; et al
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Additional info for A review of the literature published between September 1979 and August 1980
29) that the piperitone photo-adduct (209) undergoes a thermal rearrangement to produce (210). These authors have now shown that (210) can be converted into calameon (see also Ref. 228). loO As shown in Scheme 26, the critical synthetic step involves the solvolysis of the bicyclic tosylate (213) which proceeds by intramolecular capture of the cyclopropylcarbinyl cation by the pendant acetylene group to afford (214). 96 97 98 99 loo F. E. Condon and D. L. West, J. Org. , 1980,45,2006. P. A. Wender and J.
86 Previously these two compounds have been converted into (+)-zizaene (189). 0'*5]undecyl skeleton involves the intramolecular 1 iii-v, - - 0 vi, vii viii-x PhS* i PhS' OTs 1 x i . SMe,; ix, H,O,-OH-; x, TsCI-py ; xi, MCPBA; xii, KOBu'; xiii, Na-Hg-Na2HP04; xiv, (CO,H),-H,O; xv, NaOMe Scheme 22 " 86 L. Piovetti and A . Diara, Phytochemistry, 1977, 16, 103; L. Piovetti and A . , 1980, 21, 1453. E. Piers and J. Banville, J. Chem. , Chem. , 1979, 1138. 87aA very similar and independent result has been obtained by Oppolzer and B ~ r f o r d .
03 (224) A long standing mechanistic problem has been the route by (+)-longifolene (225) undergoes the acid-catalysed rearrangement to (-)-isolongifolene (232). Initially a mechanism was proposed in 1964 by O u r i s ~ o nwhich ' ~ ~ was attractive especially in the economy of the number of steps (225)-(232). However, in 1967 Berson and ~ o - w o r k e r spointed ~ ~ ~ out that one of the steps, (227) + (228), involved an endo- 2,3-methyl migration which lacked precedent in simpler methylnorbornyl systems.