Synthetic study of structurally complex indole terpenes total syntheses of (-)-nodulisporic acid D and (-)-nodulisporic acid C in conjunction with advanced synthetic studies towards (+)-nodulisporic acid A and (-)-nodulisporic acid B / Yike Zou.

Format:

Book

Manuscript

Thesis/Dissertation

Author/Creator:

Zou, Yike, author.

Contributor:

Smith, Amos B., degree supervisor.

Christianson, David W., degree committee member.

Dailey, William P., degree committee member.

Winkler, Jeffery D., degree committee member.

University of Pennsylvania. Department of Chemistry, degree granting institution.

Language:

English

Subjects (All):

Penn dissertations--Chemistry.

Chemistry--Penn dissertations.

Local Subjects:

Penn dissertations--Chemistry.

Chemistry--Penn dissertations.

Physical Description:

2 volumes (xiii, 595 leaves) : illustrations ; 29 cm

Production:

[Philadelphia, Pennsylvania] : University of Pennsylvania, 2018.

Summary:

The first total syntheses of architecturally complex indole terpenes (-)-nodulisporic acid D and (-)-nodulisporic acid C are reported here via a unified strategy of late-stage union of large fragments. Key synthetic transformations in the total synthesis of (-)-nodulisporic acid D comprise vicinal difunctionalization of an advanced [alpha],[beta]-unsaturated aldehyde to form the trans-fused 5,6-ring system in the eastern hemisphere and a palladium mediated cascade cross-coupling/indolization protocol leading to a multi-substituted indole core. Key synthetic transformations in the total synthesis of (-)-nodulisporic acid C venture include a Nozaki-Hiyama-Kishi reaction leading to a tricyclic western hemisphere intermediate, a late stage tert-butyl carbamate directed ortho-lithiation/prenylation, and a palladium catalyzed cascade cross coupling/indole formation.

Notes:

Ph. D. University of Pennsylvania 2018.

Department: Chemistry.

Supervisor: Amos B. Smith.

Includes bibliographical references.