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Sporolide B: Synthetic Studies.

Jeffery A Gladding¹, James P Bacci, Scott A Shaw

¹Department of Chemistry, Monell Chemical Senses Center and Laboratory of Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, United States.

|October 25, 2011

Summary

Researchers explored the synthesis of the marine natural product sporolide B. Despite successfully joining key fragments and achieving macrocyclization, steric hindrance prevented the formation of the target molecule.

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Area of Science:

Organic Chemistry
Natural Product Synthesis
Marine Natural Products

Background:

Sporolide B is an architecturally complex marine natural product.
The synthesis of complex natural products presents significant challenges in organic chemistry.

Purpose of the Study:

To describe studies directed towards the synthesis of sporolide B.
To investigate strategies for assembling advanced synthetic fragments of sporolide B.

Main Methods:

Retrosynthetic analysis to identify key fragments (hydroquinone and benzodiquinane).
Fragment elaboration and coupling via ester linkage.
Macrocyclization studies to form the final ring structure.

Main Results:

Successful synthesis and coupling of advanced hydroquinone and benzodiquinane fragments.
Formation of a novel macrocyclization product.
Identification of steric hindrance at tertiary hydroxyls (C6 and C10) as a barrier to sporolide B formation.

Conclusions:

The synthetic strategy successfully assembled key fragments of sporolide B.
Steric encumbrance of specific hydroxyl groups impedes the final macrocyclization step for sporolide B.
Further synthetic modifications may be required to overcome steric challenges in future sporolide B synthesis efforts.