Total Synthesis of (−)‐Merochlorin A

The first asymmetric total synthesis of the meroterpenoid (−)‐merochlorin A is described, leading to the assignment of the previously undetermined absolute configuration.

Abstract

The first asymmetric total synthesis of the meroterpenoid (−)‐merochlorin A is described. The route features enantiospecific gold‐catalyzed tandem 1,3‐acyloxy migration/Nazarov/aldol reaction sequence to furnish the bicyclo[3.3.0]octane core in a single step from a linear propargylic 1,3‐enyne aldehyde. After completion of the central skeleton by reductive enol lactone rearrangement, late stage Diels–Alder cycloaddition/aromatization sequence installed the resorcinol. An additional salient feature of the synthesis is the assignment of the absolute configuration, which had not been determined previously.

from A via a.sfakia on Inoreader http://bit.ly/2QMy3ii