By A. Furstner
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Additional resources for Active Metals [chemistry]
We have recently reported an extension of this methodology in the production of spiro-d-lactones . Much work has been done to elucidate novel synthetic routes for these types of molecules . In particular, d-substituted d-lactones have recently attracted considerable attention, mainly because molecules of this class include many natural products that exhibit significant biological activity . Scheme 1-9 illustrates a route for the synthesis of spiro d-lactones from the magnesium complex of 1,2-bis(methylene)cyclohexane 1 .
Typically, a 1 ,n-dibromoalkane was added to the THF solution of the diene-magncsium complex at -78 "C,producing an organomagnesium intermediate accommodating a bromo group. The intermediate cyclized upon warming, affording the corresponding spirocarbocycle containing an exocyclic double bond. A wide variety of spirocycles were synthesized from the reactions of magnesium complexes of 1,2-dimethylenecyclopentane and 1,2-dimethylenecycloheptane with 1,n-dibromoalkanes as shown in Table 1-4. Therefore, this spiroannulation method provides a very general approach to a large number of spirocarbocycles with different combinations of ring sizes.
2 Kiekr Mugtwsiiitn. Culcium, Strorr/ium, cind Rurirrin 15 intermediate. 2. S]oct-l -yl acctate, 7. Upon basic work-up, thc spiroacetatc 7 also afforded the /j,y-unsaturdted ketone product, 6. It is important to notc that the ring enlargement from 2 to 3 involves a vinylcyclopropane-cyclopcntenc ling expansion which has also bccn observed for thc lithium salts of 2vinylcyclopropanol systems (311. On the other hand, the rearrangement of 5 to 6 is formally a 2-vinylcyclopropanol ring opening with a proton transfer.