“…of Me2AlCl ( IM s o h in hexane, Aldrich ; 1100 ml) was added dropwise within 10 min to a stirred soln. of 2 [4] (20 g, 0.085 mol) in 1,2-dichloroethane (180 ml) at r. t. under N,. The soln.…”
Section: Experimental Partmentioning
confidence: 99%
“…The use of the stronger Lewis acids, MeAIC1, or EtAICl,, in CH,CI, at r. t., produced complex mixtures containing only small amounts ( < 5%) of 3. 4 …”
(±)‐Muscone ((±)‐1) has been synthesised in three steps from 2‐(2′‐methylprop‐2′‐enyl)cyclododecan‐1‐one (2). The synthesis involves two key transformations: a Lewis‐acid‐mediated intramolecular ene reaction (2→3) and the β‐cleavage of the bicyclic potassium alkoxide 3a′ to the macrocyclic enone (Z)‐11.
“…of Me2AlCl ( IM s o h in hexane, Aldrich ; 1100 ml) was added dropwise within 10 min to a stirred soln. of 2 [4] (20 g, 0.085 mol) in 1,2-dichloroethane (180 ml) at r. t. under N,. The soln.…”
Section: Experimental Partmentioning
confidence: 99%
“…The use of the stronger Lewis acids, MeAIC1, or EtAICl,, in CH,CI, at r. t., produced complex mixtures containing only small amounts ( < 5%) of 3. 4 …”
(±)‐Muscone ((±)‐1) has been synthesised in three steps from 2‐(2′‐methylprop‐2′‐enyl)cyclododecan‐1‐one (2). The synthesis involves two key transformations: a Lewis‐acid‐mediated intramolecular ene reaction (2→3) and the β‐cleavage of the bicyclic potassium alkoxide 3a′ to the macrocyclic enone (Z)‐11.
“… and later by a number of other groups, indicating its importance as a musk; the first total synthesis of the active enantiomer, ( R )-(+)-muscopyridine, was reported in 1982, but more recently, syntheses have been reported 5 with ring-closing metathesis as the key step. Structural isomers of muscopyridine have also been prepared in studies on structure−odor relationships on this valuable family. 1 …”
[reaction: see text] Muscothiazoles A (2b) and B (2c) have been prepared by two approaches that differ in the order of assembly of the rings. Comparative studies show that substitution of the carbon chains in substrate 5 or 12 (respective precursors to 13-membered and 14-membered rings by RCM), even by a single methyl group, can have a profound effect on increasing the efficiency of the macrocyclization.
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