Formal total synthesis of pseudopteroxale. Progress toward total synthesis of hamigeran B

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Formal total synthesis of pseudopteroxale. Progress toward total synthesis of hamigeran B

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Title: Formal total synthesis of pseudopteroxale. Progress toward total synthesis of hamigeran B
Author: Cai, Zhengxin
Keywords: synthetic organic chemistry
natural product synthesis
Hamigera tarangaensis
hamigeran B
bioactivity
Date: 2011
Publisher: University of Missouri--Columbia
Abstract: In the first chapter, a formal total synthesis of pseudopteroxazole is presented, highlightening an E-selective Horner-Emmons reaction, a Buchwald-Hartwig coupling, and a diastereoselective intramolecular Michael addition. In the second chapter, the effort toward synthesizing anti-viral natural product hamigeran B is summarized. Several routes to the core structure were shown separately, including those unexpected discoveries when pursuing those routes. Tius-Nazarov cyclization was first applied in synthesizing natural product; an efficient palladiumcatalyzed oxidative intramolecular carbocyclization was realized on an α-hydroxy enone for the first time; an interrupted Nazarov cyclization of a hydrolysis intermediate of dithiane was achieved.
URI: http://hdl.handle.net/10355/14284
Other Identifiers: CaiZ-072911-D195

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