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Synthesis 2003(9): 1427-1432
DOI: 10.1055/s-2003-40195
DOI: 10.1055/s-2003-40195
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York
Stereoselective Synthesis of Novel Ptilomycalin A Analogs via Successive 1,3-Dipolar Cycloaddition Reactions and their Ca2+-ATPase Inhibitory Activity
Further Information
Publication History
Received
5 May 2003
Publication Date:
24 June 2003 (online)


Abstract
The pentacyclic guanidine compounds 4 and 5 were stereoselectively synthesized as novel ptilomycalin A and crambescidin analogs. The synthetic method involves successive 1,3-dipolar cycloaddition reactions which effectively access the key intermediates, trans- and cis-2,5-disubstituted pyrrolidine 8 having hydroxyl groups at the β-positions on their side chains. Among the analogs synthesized, 4b and 5b exhibited significant inhibitory activity against Ca2+-ATPase.
Key Words
ptilomycalin A - 1,3-dipolar cycloaddition - nitrone - pentacyclic guanidine - Ca2+-ATPase inhibitory activity