By J R Hanson; R B Boar; Royal Society of Chemistry.; et al
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Extra resources for A review of the literature published between September 1979 and August 1980
K. Han, J. Org. , 1979,44, '4014. S . Chatterjee, J. Chem. , Chem. , 1979,620. M . C. Pirrung, J. A m . Chem. ,1979,101,7130.
G. (243). As a result of degradation/mass spectral studies this was shown not to be the case and hence the implication of longicyclene seemed to be untenable. D However, in a nice example of carrying out one too many experiments (in an effort to intercept possible intermediates in the rearrangement), longifolene was treated with D,PO,-dioxan. Under these conditions isolongifolene incorporated almost double the number of deuterium atoms as under the previous conditions and degradation/mass spectral studies clearly indicated the involvement of longicyclene (indeed longicyclene is formed in up to 20% in this process after a certain time interval).
Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochernistry, 1980, 19, 579. 148Two memorable syntheses of isocomene (321) have been reported. The first one (Scheme 38) by Paquette and Han149relies upon a successful cyclopentane annulation of the bicyclic enone (331). 1soThe second synthesis (Scheme 39) by PirrunglS1is ingenious in its economy of steps hinging upon a high-yield intramolecular photochemical addition. c" * i &* .. % 1 (3311 iv, v (321) Reagents: i, [ z p M g B r - C u B r - S M e 2 ; Cr0,-H'; ii, MeLi; iii, SOC1,-py; iv, H,O'; v, SnCl,; vi, vii, LDA; viii, PhSeCl; ix, MCPBA; x, A; xi, Me,CuLi; xii, N2H,-K2C0,, A Scheme 38 @ ** L @ % & O (321) Reagents: i, LDA; ii, MeI; iii, L M g B r ; iv, H 3 0 + ;V, h v ; vi, CH,=PPh,; vii, PTSA Scheme 39 14' 149 151 R.
A review of the literature published between September 1979 and August 1980 by J R Hanson; R B Boar; Royal Society of Chemistry.; et al