Enantiospecific gram scale synthesis of (S)-eleagnine

Enantiospecific synthesis of pacifigorgianes

Pacifigorgianes 1 are a small group of sesquiterpenes, containing bicyclo[4.3.0]nonane moiety, found to be present in both marine and terrestrial sources. The first member of this group, ichthyotoxic (+)pacifigorgiol 2 was isolated in 1982 by the research groups of Fenical and Clardy 1 from the pacific gorgonian coral Pacifigorgia cf. adamssi. Later in 1986, Simpa and coworkers 2 reported the i...

Gram-scale synthesis of iejimalide B.

Iejimalide B (2) is the most promising member of a small family of marine polyene macrolides endowed with remarkably selective activity against human cancer cell lines. As this product, however, is hardly available from the natural sources, a detailed evaluation requires the development of an efficient and practical synthetic approach. This challenge has now been met by adapting the first total...

Enantiospecific formal total synthesis of (+)-fawcettimine.

The diastereospecific attack of the silyl enol ether on the activated cyclopropyl diester 27 generated the hydrindanone 28 with complete stereocontrol. Thermal decarbomethoxylation of 28 gave the monoester 29, a key intermediate in Heathcock's synthesis, thereby completing a formal total synthesis of (+)-fawcettimine 1. The analogous cyclization of 33, the diastereomer of 27, afforded the diast...

Enantiospecific first total synthesis of cucumin-H

Concise Enantiospecific Total Synthesis of Tubingensin A

We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.