Abstract
The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO2H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolidinone stereochemistry of both compounds was confirmed by synthesizing epimers of the proposed structures. The spectroscopic data of these epimers were in complete agreement with those for the naturally derived material.
Highlights
The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described
Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling and Blaise reaction
Microsclerodermins A–I were isolated by Faulkner and co-workers from the marine sponges Microscleroderma and Theonella between 1994 and 2000.[1]. In 2012, Li and co-workers reported the structures of microsclerodermins J and K, isolated from the marine sponge Microscleroderma herdmani,[2] as well as the concomitant isolation of microsclerodermins A and B
Summary
The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. The R configuration of the pyrrolidinone stereocenter of microsclerodermin E was confirmed by total synthesis.[4]
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