Stereocontrolled Total Synthesis of (+)‐Streptazolin by a Palladium‐Catalyzed Reductive Diyne Cyclization

Abstract

(+)‐Streptazolin synthesis revisited: The key reaction in the 11‐step total synthesis of (+)‐streptazolin (3), which starts from D‐mannitol diacetonide, is the palladium‐catalyzed reductive cyclization of two alkyne arms in 1 to provide the desired 1,3‐diene 2 with the correct defined geometry. TBS=tert‐butyldimethylsilyl.

Oxazolidin-2-one Ring, a Popular Framework in Synthetic Organic Chemistry: Part 1. The Construction of the Oxazolidin-2-one Ring

“…An efficient, atom-economical [142] preparation of (+)-streptazolin, based on a palladium-catalyzed reductive diyne cyclization as the key step, has been reported by Trost [143] (Scheme 102).…”

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

“…A palladium-catalyzed reductive cyclization reaction of a diyne was used as the key step in the synthesis of (+)-streptazolin [85] (Scheme 69).…”

The streptazolin- and obscurolide-type metabolites from soil-derivedStreptomyces albonigerYIM20533 and the mechanism of influence of γ-butyrolactone on the growth ofStreptomycesby their non-enzymatic reaction biosynthesis

“…8,9 Some synthesis research on the compound and its analogues has also been developed. [10][11][12] Recent research has proved that the compound can also increase bacterial killing and elaboration of immunostimulatory cytokines by macrophages. 13 The diene and oxazolidinone moieties are considered as the pharmacophore in streptazolin and its analogues.…”