Abstract
A concise and versatile syntheses of 11-16-membered macrolides
and 13-15-membered macrolactams have been achieved using
a Tsuji-Trost type reaction. This approach is composed
of intramolecular cyclization employing ethyl carbonate with carboxylic
acids and catalytic amount of Pd(PPh3 )4 to
form carbon-heteroatom covalent bonds with no use of stoichiometric
reagents.
Key words
macrolactones - macrolactams - palladium-catalyzed reaction - carbon-heteroatom bond formation
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the isolated single (E )-α-7c under the same reaction conditions afforded
a 90:10 mixture of E /Z -isomers without production of γ-7c (Scheme
[4 ]
).
Scheme 4
11 This would be attributed to the strain
based on the ring size.
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13 The macrolactamization of 9c in the absence of KOt -Bu resulted
in α-12c in 44% yield
(Scheme
[5 ]
).
Scheme 5