Total Synthesis of Sphingofungin E and 4,5-Di-epi-sphingofungin E

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Natural Product Synthesis

Background:

• Sphingofungins are a class of bioactive natural products with potential pharmaceutical applications.
• Previous synthetic efforts have focused on related compounds like myriocin and mycestericin D.
• Stereoselective synthesis of complex polyketide-derived natural products remains a significant challenge in organic chemistry.

Purpose of the Study:

• To achieve the total synthesis of sphingofungin E.
• To synthesize the 4,5-di-epi-sphingofungin E stereoisomer.
• To explore the utility of a common intermediate for the synthesis of related natural products.

Main Methods:

• Utilized a shared synthetic intermediate previously employed in the synthesis of myriocin and mycestericin D.
• Employed antipodal stereoselective dihydroxylations to establish key stereocenters.
• Developed a convergent synthetic strategy for efficient assembly of the target molecules.

Main Results:

• Successfully synthesized sphingofungin E.
• Successfully synthesized 4,5-di-epi-sphingofungin E.
• Demonstrated the versatility of the common intermediate in accessing diverse sphingofungin analogs.

Conclusions:

• The total synthesis of sphingofungin E and 4,5-di-epi-sphingofungin E was successfully accomplished.
• The synthetic route highlights the effectiveness of antipodal stereoselective dihydroxylations.
• The study provides a valuable platform for accessing other sphingofungin derivatives and analogs.