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Synfacts 2019; 15(03): 0217
DOI: 10.1055/s-0037-1611193
DOI: 10.1055/s-0037-1611193
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (–)-Sinulariadiolide
Further Information
Publication History
Publication Date:
15 February 2019 (online)
Key words
(–)-sinulariadiolide - Eschenmoser–Tanabe fragmentation - ring-closing alkyne metathesis - trans-hydrostannation - Michael addition![](https://www.thieme-connect.de/media/synfacts/201903/i_c004_s1_10-1055_s-0037-1611193.gif)
Significance
The tricyclic nor-cembranoid sinulariadiolide was first isolated in 1996 from soft corals found in Okinawa. Fürstner and Meng report the total synthesis of (–)-sinulariadiolide via ring-closing alkyne metathesis followed by an intriguing intramolecular reaction cascade.
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Comment
Fragments E and H were accessed from geranic acid (A) and carvone (F). Ring-closing alkyne metathesis and hydrostannation–carbonylation of J gave N. The title compound was accessed by a sequence involving transannular Michael addition.
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