College Honors Program

Title

Synthesis of Tetrahydropyran Natural Products

Date of Creation

5-31-2023

Document Type

Campus Access Only

Department

Chemistry

First Advisor

Kevin Quinn

Abstract

Tetrahydropyrans (THPs), six-membered oxygen containing heterocycles, are common substructures of biologically and chemically important natural products. Cryptoconcatone H 1, an anti-inflammatory, and diospongin B 2, an anti-osteoporotic, are examples of tetrahydropyran natural products that are isolated from different plant species. One important difference between these targets is the stereochemical relationship between the substituents on the C2 and C6 positions of the THP. Two different synthetic strategies are presented in this thesis that allow access to both the thermodynamically preferred 2,6-cis orientation present in cryptoconcatone H, and the less synthetically available 2,6-trans orientation of diospongin B. Specifically reported is a three-step synthesis of the originally proposed structure of cryptoconcatone H, exploiting its hidden symmetry, in which the tetrahydropyran ring is constructed via Prins cyclization. In contrast, the approach to diospongin B establishes the 2,6-trans relationship in the tetrahydropyran via an oxa-Michael addition to produce a bicyclic lactone intermediate. These strategies are broadly applicable for the synthesis of an array of tetrahydropyran natural products.

Comments

Reader: Bianca Sculimbrene

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