ChemInform Abstract: The Asymmetric Synthesis of Fused Cyclopentenone Ring Systems: A Formal Asymmetric Total Synthesis of (‐)‐Isocomene.

Meyers, A. I.; Bienz, Stefan; Kwon, Hyok-Boong; Wallace, Richard H.

doi:10.1002/chin.199637123

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“…345 AC of natural (−)-capnellene 29 was established in 1990 (Scheme 12) through the synthesis of its enantiomer (+)-29. 346 Chirality found its origin in (S)-valinol 349, which was reacted with levulinic acid 350 under acid catalysis to afford the enantiomerically pure bicyclic lactam 351 (ee > 99%) in 86% yield. This lactam was next transformed in five steps and 78.2% yield into 352, which led to a mixture of the epimeric alcohols 353 and 354 through 4 steps (71.8% yield), implying reduction of the lactam part among others.…”

Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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Section: Synthesismentioning

confidence: 99%