Indole diterpenoid synthetic studies: The total synthesis of (+)-nodulisporic acid F and studies toward the total synthesis of (-)-nodulisporic acid D | Posted on:2007-07-09 | Degree:Ph.D | Type:Thesis | University:University of Pennsylvania | Candidate:Davulcu, Akin H | Full Text:PDF | GTID:2441390005463907 | Subject:Chemistry | Abstract/Summary: | | Chapter one of this dissertation provides a general introduction to the indole diterpenoid class of natural products, with an emphasis on the recently discovered nodulisporic acids. Chapter two describes the stereocontrolled total synthesis of (+)-nodulisporic acid F. Highlights of the modular synthetic strategy include an efficient anionic coupling via the Smith 2-substituted indole synthesis, an optimized C-ring annulation protocol, and a late-stage installation of the alpha,beta-unsaturated carboxylic acid sidechain via the B-alkyl Suzuki-Miyaura cross-coupling reaction.*; Chapter three details our overall strategy for the convergent, asymmetric total synthesis of (-)-nodulisporic acid D, a representative member of a recently nodulisporane class of architecturally complex indole alkaloids. In addition, we describe an expedient, stereocontrolled preparation of tricyclic western hemisphere subtarget (-)-104. Successful union of (-)- 104 with eastern hemisphere subtarget (-)-125 via our 2-substituted indole synthesis has enabled construction of the heptacyclic core of (-)-nodulisporic acid D.*; *Please refer to dissertation for diagrams. | Keywords/Search Tags: | -nodulisporic acid, Indole, Synthesis | | Related items |
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