Synthetic studies toward the total synthesis of roseophilin
Abstract
The approaches directed toward the total synthesis of Roseophilin are described. The major achievements involved are: (1) development of new synthetic methodology for the preparation of β-substituted cyclopentenone 2.12, (2) synthesis of bicyclic ketopyrrole core 1.6 via intramolecular azoene cyclization, (3 )regioselective β-isopropylation of bicyclic ketopyrrole core 1.6 using unprecedented alkylation of silyl oxycyclopentadienyl anion, (4) application of Grubbs ring-closing metathesis for the synthesis of highly strained tricyclic core derivative 4.21b, (5) synthesis of des-chloro biaryl moiety 5.10 via mercury (II) catalyzed cyclization. Finally a new synthetic strategy based on the studies for the coupling reaction of tricyclic core 1.3 is described.
Degree
Ph.D.
Advisors
Fuchs, Purdue University.
Subject Area
Organic chemistry
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