Synthetic studies of (+)-nodulisporic acid A : Development of an efficient route to Eastern Hemisphere sub-targets / Stephen S. Gonzales.

Format:

Book

Manuscript

Thesis/Dissertation

Author/Creator:

Gonzales, Stephen S.

Contributor:

Smith, Amos B., III, advisor.

University of Pennsylvania.

Language:

English

Subjects (All):

Penn dissertations--Chemistry.

Chemistry--Penn dissertations.

Local Subjects:

Penn dissertations--Chemistry.

Chemistry--Penn dissertations.

Physical Description:

xiii, 219 pages : illustrations (some color) ; 29 cm

Production:

2011.

Summary:

(+)-Nodulisporic Acid A (NsAA) is an indole diterpene of complex structure, isolated from the fungus nodulisporium sp., possessing potent insecticidal activity. Herein is described a new tactic for the construction of complex indoles employing a tandem palladium-mediated process between a haloindoline and a vinyl bromide or triflate.

Chapter 1 of this work will review the efforts by Merck and Co. that lead to the isolation and discovery of potent analogs of NsAA, as well as briefly review the history of complex indole synthesis in the Smith Research Group.

Chapter 2 will describe efforts to streamline the synthesis of the chiral, non-racemic material used to make different variants of the eastern hemisphere sub-target, the development of a new tactic for bringing the two hemispheres together, and efforts to synthesize an eastern hemisphere sub-target that contains the sidechain of NsAA.*

*Please refer to dissertation for diagrams.

Notes:

Adviser: Amos B. Smith, III.

Thesis (Ph.D. in Chemistry) -- University of Pennsylvania, 2011.

Includes bibliographical references.

OCLC:

778946935