Related Experiment Video
Updated: Aug 24, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide
Amos B Smith1, Christopher M Adams, Stephanie A Lodise Barbosa
1Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Abstract:
A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2).
More Related Videos
07:59A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation